Organic semiconductor element, manufacturing method thereof, composition for forming organic semiconductor film, compound, and organic semiconductor film

ABSTRACT

An object to be achieved by the present invention is to provide an organic semiconductor element and an organic semiconductor film having high mobility and excellent heat resistance, and a manufacturing method thereof, to provide a novel compound that is suitable as an organic semiconductor, and to provide a composition for forming an organic semiconductor film in which coating film formability is excellent, with which an organic semiconductor element that has high mobility can be obtained, and in which heat resistance is excellent, an organic semiconductor element in which the composition for forming an organic semiconductor film is used, and a manufacturing method thereof. 
     The organic semiconductor element according to the present invention includes a compound represented by Formula 1 below included in an organic semiconductor layer.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation application of International Application No. PCT/JP2015/082668, filed Nov. 20, 2015, the disclosure of which is incorporated herein by reference in its entirety. Further, this application claims priority from Japanese Patent Application No. 2014-237888, filed Nov. 25, 2014, the disclosure of which is incorporated herein by reference in its entirety.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to an organic semiconductor element, a manufacturing method thereof, a composition for forming an organic semiconductor film, a compound, and an organic semiconductor film.

2. Description of the Related Art

An organic transistor having an organic semiconductor film (organic semiconductor layer) is used in a field effect transistor (FET) used in a liquid crystal display or an organic electroluminescence (EL) display, Radio Frequency Identifier (RFID, RF tag), and the like, because lightening of weight, cost reduction and flexibilization can be achieved.

As the organic semiconductor in the related art, those disclosed in JP2010-177637A and WO2013/168048A are known.

SUMMARY OF THE INVENTION

An object to be achieved by the present invention is to provide an organic semiconductor element and an organic semiconductor film having high mobility and excellent heat resistance, and a manufacturing method thereof.

Another object to be achieved by the present invention is to provide a novel compound that is suitable as an organic semiconductor.

Still another object to be achieved by the present invention is to provide a composition for forming an organic semiconductor film in which coating film formability is excellent, with which an organic semiconductor element that has high mobility can be obtained, and in which heat resistance is excellent, an organic semiconductor element in which the composition for forming an organic semiconductor film is used, and a manufacturing method thereof.

The objects of the present invention are solved by the means described in <1>, <17>, <34>, <35>, <37>, <38>, and <40> below. <1> to <16>, <18> to <33>, <36>, and <39> which are preferable embodiments are also described below.

<1> An organic semiconductor element comprising: a compound represented by Formula 1 below in an organic semiconductor layer,

in Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom, Z^(1a) to Z^(1j) each independently represent a hydrogen atom or a halogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom, R^(A11) represents a hydrogen atom or a group represented by R¹¹, A¹² represents ═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogen atom or a group represented by R¹², n1 represents 0 or 1, p1 represents an integer of 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0 or 1 in a case where A¹¹ is a nitrogen atom, q1 represents an integer of 0 to 2 in a case where A¹² is ═CR^(A12)— and represents 0 or 1 in a case where A¹² is a nitrogen atom, R¹¹ and R¹² each independently represent a halogen atom, an aryl group, a heteroaryl group, or a group represented by Formula W below, and

-S^(W)-L^(W)-T^(W)  (W)

in Formula W, S^(W) represents a single bond or an alkylene group represented by —(CR^(S) ₂)_(k)—, R^(S) each independently represent a hydrogen atom or a halogen atom, k represents an integer of 1 to 17, L^(W) represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-16 below, or a group obtained by bonding any two or more of divalent linking groups represented by Formulae L-1 to L-16 below, T^(W) represents an alkyl group, a cyano group, a vinyl group, an ethynyl group, an aryl group, a heteroaryl group, an oxyethylene group, an oligooxyethylene group of which the repetition number of oxyethylene units is two or greater, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group,

in Formulae L-1 to L-16, * and wavy line portions represent bonding positions to other structures, p13 represents an integer of 0 to 4, p14, p15, and p16 each independently represent an integer of 0 to 2, R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) each independently represent a hydrogen atom or a substituent.

<2> The organic semiconductor element according to <1>, in which all of Z^(1a) to Z^(1j) are hydrogen atoms.

<3> The organic semiconductor element according to <1> or <2>, in which n1 is 0.

<4> The organic semiconductor element according to any one of <1> to <3>, in which at least one of p1 or q1 is not 0.

<5> The organic semiconductor element according to any one of <1> to <4>, in which at least one of p1 or q1 is not 0, and at least one of R¹¹ or R¹² is a group represented by Formula W.

<6> The organic semiconductor element according to any one of <1> to <5>, in which p1 and q1 are 1.

<7> The organic semiconductor element according to any one of <1> to <6>, in which both of X¹¹ and X¹² are S atoms, A¹¹ is ═CR^(A11)—, and A¹² is ═CR^(A12)—.

<8> The organic semiconductor element according to any one of <1> to <6>, in which a compound represented by Formula 1 is a compound represented by Formula 2 below,

in Formula 2, X²¹ and X²² each independently represent a chalcogen atom, W²¹ and W²² each independently represent a group represented by Formula W.

<9> The organic semiconductor element according to any one of <1> to <8>, in which the compound represented by Formula 1 is a line symmetric structure.

<10> The organic semiconductor element according to any one of <1> to <9>, in which the number of carbon atoms in the group represented by Formula W is 5 to 40.

<11> The organic semiconductor element according to any one of <1> to <10>, in which L^(W) is a single bond, a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16, or a divalent linking group obtained by bonding two or more divalent linking groups represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.

<12> The organic semiconductor element according to any one of <1> to <11>, in which L^(W) is a single bond or a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.

<13> The organic semiconductor element according to any one of <1> to <12>, in which S^(W) is a single bond.

<14> The organic semiconductor element according to any one of <1> to <13>, in which L^(W) is a single bond or a divalent linking group represented by any one of Formula L-1 and Formulae L-13 to L-16.

<15> The organic semiconductor element according to any one of <1> to <14>, in which T^(W) is an alkyl group.

<16> The organic semiconductor element according to any one of <1> to <15>, in which a group represented by Formula W is an alkyl group.

<17> A composition for forming an organic semiconductor film, comprising: a solvent having a boiling point of 100° C. or higher; and a compound represented by Formula 1, in which a content of the compound represented by Formula 1 is 20 mass % or less with respect to a total amount of the composition for forming an organic semiconductor film.

<18> The composition for forming an organic semiconductor film according to <17>, in which all of Z^(1a) to Z^(1j) are hydrogen atoms.

<19> The composition for forming an organic semiconductor film according to <17> or <18>, in which n1 is 0.

<20> The composition for forming an organic semiconductor film according to any one of <17> to <19>, in which at least one of p1 or q1 is not 0.

<21> The composition for forming an organic semiconductor film according to any one of <17> to <20>, in which at least one of p1 or q1 is not 0, and at least one of R¹¹ or R¹² is a group represented by Formula W.

<22> The composition for forming an organic semiconductor film according to any one of <17> to <21>, in which p1 and q1 is 1.

<23> The composition for forming an organic semiconductor film according to any one of <17> to <22>, in which both of X¹¹ and X¹² are S atoms, A¹¹ is ═CR^(A11)—, and A¹² is ═CR^(A12)—.

<24> The composition for forming an organic semiconductor film according to any one of <17> to <22>, in which the compound represented by Formula 1 is a compound represented by Formula 2.

<25> The composition for forming an organic semiconductor film according to any one of <17> to <24>, in which the compound represented by Formula 1 is a line symmetric structure.

<26> The composition for forming an organic semiconductor film according to any one of <17> to <25>, in which the number of carbon atoms in the group represented by Formula W is 5 to 40.

<27> The composition for forming an organic semiconductor film according to any one of <17> to <26>, in which L^(W) is a single bond, a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16, and a divalent linking group obtained by bonding two or more divalent linking groups represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.

<28> The composition for forming an organic semiconductor film according to any one of <17> to <27>, in which L^(W) is a single bond or a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.

<29> The composition for forming an organic semiconductor film according to any one of <17> to <28>, in which S^(W) is a single bond.

<30> The composition for forming an organic semiconductor film according to any one of <17> to <29>, in which L^(W) is a single bond or a divalent linking group represented by any one of Formula L-1 and Formulae L-13 to L-16.

<31> The composition for forming an organic semiconductor film according to any one of <17> to <30>, in which T^(W) is an alkyl group.

<32> The composition for forming an organic semiconductor film according to any one of <17> to <31>, in which a group represented by Formula W is an alkyl group.

<33> The composition for forming an organic semiconductor film according to any one of <17> to <32>, further comprising: a binder polymer, in which a content of the binder polymer is 10 mass % or less with respect to a total amount of the composition for forming an organic semiconductor film.

<34> A compound represented by Formula 1.

<35> A method of manufacturing an organic semiconductor film, comprising: an applying step of applying the composition for forming an organic semiconductor film according to any one of <17> to <33> to a substrate, and a removing step of removing at least a portion of the solvent having a boiling point of 100° C. or higher included in the composition for forming an organic semiconductor film.

<36> The method of manufacturing the organic semiconductor film according to <35>, in which the applying step is performed by an ink jet method or a flexographic printing method.

<37> An organic semiconductor film obtained by the method according to <35> or <36>.

<38> A method of manufacturing an organic semiconductor element, comprising: an applying step of applying the composition for forming an organic semiconductor film according to any one of <17> to <33> to a substrate, and a removing step of removing at least a portion of the solvent having a boiling point of 100° C. or higher included in the composition for forming an organic semiconductor film.

<39> The method of manufacturing the organic semiconductor element according to <38>, in which the applying step is performed by an ink jet method or a flexographic printing method.

<40> An organic semiconductor element manufactured by the method according to <38> or <39>.

According to the present invention, it is possible to provide an organic semiconductor element and an organic semiconductor film having high mobility and excellent heat resistance, and a manufacturing method thereof.

According to the present invention, it is possible to provide a novel compound that is suitable as an organic semiconductor.

According to the present invention, it is possible to provide a composition for forming an organic semiconductor film in which coating film formability is excellent, with which an organic semiconductor element that has high mobility can be obtained, and in which heat resistance is excellent, an organic semiconductor element in which the composition for forming an organic semiconductor film is used, and a manufacturing method thereof.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic cross-sectional view of an aspect of an organic semiconductor element of the present invention.

FIG. 2 is a schematic cross-sectional view of another aspect of the organic semiconductor element of the present invention.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, the contents of the present invention will be specifically described. The constituents in the following description will be explained based on typical embodiments of the present invention, but the present invention is not limited to the embodiments. In the specification of the present application, “to” is used to mean that the numerical values listed before and after “to” are a lower limit and an upper limit respectively. Furthermore, in the present invention, an organic EL element refers to an organic electroluminescence element.

In the present specification, in a case where there is no description regarding whether a group (atomic group) is substituted or unsubstituted, the group includes both of a group having a substituent and a group not having a substituent. For example, an “alkyl group” includes not only an alkyl group not having a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).

In the present specification, in some cases, a chemical structural formula is described as a simplified structural formula in which a hydrogen atom is omitted.

In the present invention, “mass %” and “weight %” have the same definition, and “part by mass” and “part by weight” have the same definition.

In the present invention, a combination of preferred aspects is more preferable.

(Organic Semiconductor Element and Compound)

The organic semiconductor element according to the present invention includes a compound (hereinafter, referred to as a “specific compound”) represented by Formula 1 above in an organic semiconductor layer.

The compound represented by Formula 1 above is preferably an organic semiconductor compound.

As a result of diligent research, the present inventors found that an organic semiconductor element or an organic semiconductor film containing the compound represented by Formula 1 has high mobility and excellent heat resistance, so as to complete the present invention.

A specific mechanism for exhibiting the effect is not clear, but it is assumed that if the compound represented by Formula 1 has line symmetry with a molecular center as an axis of symmetry in a certain degree or greater, mobility improves since crystallinity becomes excellent, and heat resistance of the organic semiconductor element is improved since a melting point increases.

It is assumed that crystallinity is excellent and mobility is improved, since the compound represented by Formula 1 has a molecular shape that the terminal thiophene ring protrudes from a rod-like structure such as a phenanthrene structure or a picene structure, and the appearance of a liquid crystal layer is suppressed. The mechanism of the suppression of the appearance of the liquid crystal layer as above contributes to the improvement of the heat resistance of the organic semiconductor element.

<Specific Compound>

The specific compound according to the present invention is represented by Formula 1 below.

In Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom, Z^(1a) to Z^(1j) each independently represent a hydrogen atom or a halogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom, R^(A11) represents a hydrogen atom or a group represented by R¹¹, A¹² represents ═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogen atom or a group represented by R¹², n1 represents 0 or 1, p1 represents an integer of 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0 or 1 in a case where A¹¹ is a nitrogen atom, q1 represents an integer of 0 to 2 in a case where A¹² is ═CR^(A12)— and represents 0 or 1 in a case where A¹² is a nitrogen atom, R¹¹ and R¹² each independently represent a halogen atom, an aryl group, a heteroaryl group, or a group represented by Formula W below.

-S^(W)-L^(W)-T^(W)  (W)

In Formula W, S^(W) represents a single bond or an alkylene group represented by —(CR^(S) ₂)_(k)—, R^(S) each independently represent a hydrogen atom or a halogen atom, k represents an integer of 1 to 17, L^(W) represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-16 below, or a group obtained by bonding any two or more of divalent linking groups represented by Formulae L-1 to L-16 below, T^(W) represents an alkyl group, a cyano group, a vinyl group, an ethynyl group, an aryl group, a heteroaryl group, an oxycthylene group, an oligooxycthylene group of which the repetition number of oxyethylene units is two or greater, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group.

In Formulae L-1 to L-16, * and wavy line portions represent bonding positions to other structures, p13 represents an integer of 0 to 4, p14, p15, and p16 each independently represent an integer of 0 to 2, R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) each independently represent a hydrogen atom or a substituent.

The specific compound according to the present invention is preferably an organic semiconductor compound.

The specific compound according to the present invention is a novel compound.

The specific compound according to the present invention can be suitably used for an organic semiconductor element, an organic semiconductor film, and a composition for forming an organic semiconductor film.

In Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom, it is preferable that X¹¹ and X¹² each independently represent an O atom or an S atom, and it is more preferable that both of X¹¹ and X¹² are S atoms. The chalcogen atom refers to an atom in Group 16 including an O atom.

Z^(1a) to Z^(1j) each independently represent a hydrogen atom or a halogen atom, and it is preferable that all of Z^(1a) to Z^(1j) are hydrogen atoms.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.

A¹¹ represents ═CR^(A11)— or an nitrogen atom, and ═CR^(A11)— is preferable.

R^(A11) represents a hydrogen atom or a group represented by R¹¹, and a hydrogen atom is preferable. The expression “R^(A11) represents a group represented by R¹¹” refers to a case where one of R¹¹'s of which the number is specified by p1 in Formula 1 is bonded to a carbon atom in A¹¹.

A¹² represents ═CR^(A12)— or a nitrogen atom, and ═CR^(A12)— is preferable.

R^(A12) represents a hydrogen atom or a group represented by R¹², and a hydrogen atom is preferable. The expression “R^(A12) represents a group represented by R¹²” refers to a case where one of R¹²'s of which the number is specified by q1 in Formula 1 is bonded to a carbon atom in A².

n1 represents 0 or 1 and preferably 0.

In a case where A¹¹ is ═CR^(A11)—, p1 represents an integer of 0 to 2, preferably represents 1 or 2, more preferably 1. In a case where A¹¹ is a nitrogen atom, p1 represents 0 or 1 and preferably represents 1. In a case where A¹¹ is ═CR^(A11)—, and p1 is 1, R¹¹ is preferably bonded to a carbon atom positioned between A¹¹ and X¹¹, not a carbon atom included in A¹¹.

In a case where A¹² is ═CR^(A12)—, q1 represents an integer of 0 to 2, preferably represents 1 or 2, and more preferably represents 1. In a case where A¹² is a nitrogen atom, q1 represents 0 or 1 and preferably represents 1. In a case where A¹² is ═CR^(A12)— and q1 is 1, R¹² is preferably bonded to a carbon atom positioned between A¹² and X¹², not a carbon atom included in A¹².

R¹¹ and R¹² each independently represent a halogen atom, an aryl group, a heteroaryl group, or a group represented by Formula W below and preferably represents a group represented by Formula W.

-S^(W)-L^(W)-T^(W)  (W)

In Formula W, S^(W) represents a single bond or an alkylene group represented by —(CR^(S) ₂)_(k)— and preferably represents a single bond.

R^(S) each independently represent a hydrogen atom or a halogen atom and preferably a hydrogen atom.

k represents an integer of 1 to 17, preferably represents an integer of 1 to 15, and more preferably an integer of 1 to 10.

L^(W) represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-16, or a group obtained by bonding any two or more of divalent linking groups represented by Formulae L-1 to L-16, preferably represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16, or a divalent linking group obtained by bonding two or more divalent linking groups represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16, more preferably a single bond or a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16, and even more preferably a divalent linking group represented by any one of Formulae L-1, L-3, L-15, and L-16.

L^(W) preferably represents a single bond or a divalent linking group represented by any one of Formula L-1 and Formulae L-13 to L-16.

T^(W) represented by an alkyl group, a cyano group, a vinyl group, an ethynyl group, an aryl group, a heteroaryl group, an oxyethylene group, an oligooxyethylene group of which the repetition number of oxyethylene units is two or greater, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group.

The alkyl group is preferably an alkyl group having 2 to 18 carbon atoms, more preferably an alkyl group having 3 to 15 carbon atoms, and even more preferably an alkyl group having 4 to 13 carbon atoms. The alkyl group may have any one of a linear shape, a branched shape, or a cyclic shape, or may have a structure obtained by combining these. However, a linear or branched alkyl group is preferable, and a linear alkyl group is more preferable.

The alkyl group may be substituted and preferable examples of the substituent include a halogen atom.

Examples of the aryl group (an aromatic hydrocarbon group) include a group obtained by removing one hydrogen atom from benzene, naphthalene, anthracene, or the like. A group obtained by removing one hydrogen atom from benzene is preferable.

The aryl group may be substituted but is preferably not substituted.

Examples of a heteroatom included in a heteroaryl group (an aromatic heterocyclic group) include an oxygen atom, a nitrogen atom, and a sulfur atom. An oxygen atom and a sulfur atom are preferable, and a sulfur atom is more preferable.

Examples of the heteroaryl group include a group obtained by removing one hydrogen atom from a thiophene ring, a furan ring, a pyran ring, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a selenophene ring, an imidazole ring, and the like. A group obtained by removing one hydrogen atom from a thiophene ring or a furan ring is more preferable, and a group obtained by removing one hydrogen atom from a thiophene ring is even more preferable.

The heteroaryl group may be further substituted, but it is preferable that the heteroaryl group is not substituted.

The oligooxyethylene group of which the repetition number of oxyethylene units is two or greater is preferably an oligooxyethylene group of which the repetition number is one to five and more preferably an oligooxyethylene group of which the repetition number is one to three.

The oligosiloxane group having two or more silicon atoms is preferably an oligosiloxane group having one to five silicon atoms and more preferably an oligosiloxane group having one to three silicon atoms.

In Formulae L-1 to L-16, it is preferable that wavy line portions represent bonding positions to S^(W), * represents a bonding position to T^(W) or a bonding position to a divalent linking group selected from the group consisting of other L-1 to L-16.

p13 represents an integer of 0 to 4, p14, p15, and p16 each independently represent an integer of 0 to 2, and R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) each independently represent a hydrogen atom or a substituent.

In a case where L^(W) represents a linking group obtained by bonding a divalent linking group represented by any one of Formulae L-1 to L-16 above, the number of linkages of the divalent linking groups represented by any one of Formulae L-1 to L-16 is preferably 2 to 4 and more preferably 2 or 3.

R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) each independently represent a hydrogen atom or a substituent and preferably represent a hydrogen atom. Examples of the substituent include various substituents exemplified as T^(W) in Formula 1 above.

A plurality of R^(L1)'s, R^(L13)'s, R^(L14)'s, R^(L15)'s, and R^(L16)'s may be identical to or different from each other. R^(L1)'s, R^(L21)'s, and R^(L22)'s may form ring structures by being bonded to T^(W) adjacent to each other or may form a fused ring as the ring structure.

The group represented by Formula W is preferably an alkyl group, more preferably an alkyl group having 2 to 18 carbon atoms, even more preferably an alkyl group having 3 to 15 carbon atoms, and particularly preferably an alkyl group having 4 to 13 carbon atoms. In a case where the group represented by Formula W is an alkyl group, it is preferable that S^(W) and L^(W) are single bonds, and T^(W) is an alkyl group.

In Formula 1, it is preferable that at least one of p1 or q1 is not 0, and it is more preferable that at least one of p1 or q1 is not 0, and at least one of R¹¹ or R¹² is a group represented by Formula W.

In Formula 1, it is preferable that p1 and q1 are 1, it is more preferable that p1 and q1 are 1, and at least one of R¹¹ or R¹² is a group represented by Formula W, and it is even more preferable that p1 and q1 are 1, and both of R¹¹ and R¹² are groups represented by Formula W.

In Formula 1, it is preferable that both of X¹¹ and X¹² are S atoms, A¹¹ is ═CR^(A11)—, and A¹² is ═CR^(A12)—, it is more preferable that both of X¹¹ and X¹² are S atoms, A¹¹ is ═CR^(A11)—, A¹² is ═CR^(A12)—, and both of R^(A11) and R^(A12) are hydrogen atoms.

The compound represented by Formula 1 is preferably a compound represented by Formula 2 below.

In Formula 2, X²¹ and X²² each independently represent a chalcogen atom, preferably an O atom or a S atom. It is more preferable that both of X²¹ and X²² are S atoms. W²¹ and W²² each independently represent a group represented by Formula W above, and a preferable aspect thereof is the same as the preferable aspect described in the group represented by Formula W above.

The compound represented by Formula 1 above is preferably a line symmetric structure.

The expression “a compound has a line symmetric structure” means that a structural formula thereof is line symmetric with respect to the entire molecule. Specifically, the compound represented by Formula 1 is preferably a compound represented by Formulae 3 to 5 below.

It is considered that, if the compound represented by Formula 1 has a line symmetric structure, crystallinity and melting point become high, and mobility or heat resistance of an obtained organic semiconductor element or an obtained organic semiconductor film increase.

In Formula 3 or 4, X¹¹, X¹², Z^(1a) to Z^(1j), A¹¹, A¹², p1, q1, R¹¹, and R¹² have the same meaning as X¹¹, X¹², Z^(1a) to Z^(1j), A¹¹, A¹², p1, q1, R¹¹, and R¹² in Formula 1, and preferable aspects thereof are also the same.

In Formula 5, X²¹, X²², W²¹, and W²² have the same meaning as X²¹, X²², W²¹, and W²² in Formula 2, and preferable aspects thereof are also the same.

All of the compounds represented by Formulae 3 to 5 have line symmetry having broken lines as symmetry axes.

As specific examples of the specific compound used in the present invention, Compounds 1 to 1475 represented by Formulae a to c below and presented in Tables 1 to 59 are preferably exemplified. However, the present invention is not limited thereto.

In Compounds 1 to 1475, X^(a1), X^(a2), R^(a11), R^(a12), R^(a21), R^(a22), X^(b1), X^(b2), R^(b11), R^(b12), R^(b21), R^(b22), X^(c1), X^(c2), R^(c11), and R^(c21) in Formulae a to c represent structures presented in Tables 1 to 59. In Tables 1 to 59, Ph represents a phenyl group, -Ph- represents a phenylene group, and * represents a bonding portion to another structure.

TABLE 1 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 1 S S C₄H₉—* H C₄H₉—* H Compound 2 S S C₅H₁₁—* H C₅H₁₁—* H Compound 3 S S C₆H₁₃—* H C₆H₁₃—* H Compound 4 S S C₇H₁₅—* H C₇H₁₅—* H Compound 5 S S C₈H₁₇—* H C₈H₁₇—* H Compound 6 S S C₉H₁₉—* H C₉H₁₉—* H Compound 7 S S C₁₀H₂₁—* H C₁₀H₂₁—* H Compound 8 S S C₁₁H₂₃—* H C₁₁H₂₃—* H Compound 9 S S C₁₂H₂₅—* H C₁₂H₂₅—* H Compound 10 S S C₁₃H₂₇—* H C₁₃H₂₇—* H Compound 11 S S C₁₄H₂₉—* H C₁₄H₂₉—* H Compound 12 S S C₁₅H₃₁—* H C₁₅H₃₁—* H Compound 13 S S C₁₆H₃₃—* H C₁₆H₃₃—* H Compound 14 S S C₁₇H₃₅—* H C₁₇H₃₅—* H Compound 15 S S C₁₈H₃₇—* H C₁₈H₃₇—* H Compound 16 S S C₅H₁₁—* C₅H₁₁—* C₅H₁₁—* C₅H₁₁—* Compound 17 S S C₆H₁₃—* C₆H₁₃—* C₆H₁₃—* C₆H₁₃—* Compound 18 S S C₇H₁₅—* C₇H₁₅—* C₇H₁₅—* C₇H₁₅—* Compound 19 S S C₈H₁₇—* C₈H₁₇—* C₈H₁₇—* C₈H₁₇—* Compound 20 S S C₉H₁₉—* C₉H₁₉—* C₉H₁₉—* C₉H₁₉—* Compound 21 S S C₁₀H₂₁—* C₁₀H₂₁—* C₁₀H₂₁—* C₁₀H₂₁—* Compound 22 S S C₁₁H₂₃—* C₁₁H₂₃—* C₁₁H₂₃—* C₁₁H₂₃—* Compound 23 S S C₁₂H₂₅—* C₁₂H₂₅—* C₁₂H₂₅—* C₁₂H₂₅—* Compound 24 S S C₁₃H₂₇—* C₁₃H₂₇—* C₁₃H₂₇—* C₁₃H₂₇—* Compound 25 S S C₁₄H₂₉—* C₁₄H₂₉—* C₁₄H₂₉—* C₁₄H₂₉—* Compound 26 S S C₁₅H₃₁—* C₁₅H₃₁—* C₁₅H₃₁—* C₁₅H₃₁—* Compound 27 S S C₁₆H₃₃—* C₁₆H₃₃—* C₁₆H₃₃—* C₁₆H₃₃—* Compound 28 S S C₁₇H₃₅—* C₁₇H₃₅—* C₁₇H₃₅—* C₁₇H₃₅—* Compound 29 S S C₁₈H₃₇—* C₁₈H₃₇—* C₁₈H₃₇—* C₁₈H₃₇—* Compound 30 S S p-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—* H Compound 31 S S p-C₆H₁₃—Ph—* H p-C₆H₁₃—Ph—* H Compound 32 S S p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* H Compound 33 S S p-C₈H₁₇—Ph—* H p-C₈H₁₇—Ph—* H Compound 34 S S p-C₉H₁₉—Ph—* H p-C₉H₁₉—Ph—* H Compound 35 S S p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* H Compound 36 S S p-C₁₁H₂₃—Ph—* H p-C₁₁H₂₃—Ph—* H Compound 37 S S p-C₁₂H₂₅—Ph—* H p-C₁₂H₂₅—Ph—* H Compound 38 S S p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—* H Compound 39 S S p-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* H Compound 40 S S p-C₁₅H₃₁—Ph—* H p-C₁₅H₃₁—Ph—* H Compound 41 S S p-C₁₆H₃₃—Ph—* H p-C₁₆H₃₃—Ph—* H Compound 42 S S p-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* H Compound 43 S S p-C₁₈H₃₇—Ph—* H p-C₁₈H₃₇—Ph—* H Compound 44 S S p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* Compound 45 S S p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* Compound 46 S S p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* Compound 47 S S p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* Compound 48 S S p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* Compound 49 S S p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* Compound 50 S S p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* Compound 51 S S p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—*

TABLE 2 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 52 S S p-C₁₃H₂₇—Ph-* p-C₁₃H₂₇—Ph-* p-C₁₃H₂₇—Ph-* p-C₁₃H₂₇—Ph-* Compound 53 S S p-C₁₄H₂₉—Ph-* p-C₁₄H₂₉—Ph-* p-C₁₄H₂₉—Ph-* p-C₁₄H₂₉—Ph-* Compound 54 S S p-C₁₅H₃₁—Ph-* p-C₁₅H₃₁—Ph-* p-C₁₅H₃₁—Ph-* p-C₁₅H₃₁—Ph-* Compound 55 S S p-C₁₆H₃₃—Ph-* p-C₁₆H₃₃—Ph-* p-C₁₆H₃₃—Ph-* p-C₁₆H₃₃—Ph-* Compound 56 S S p-C₁₇H₃₅—Ph-* p-C₁₇H₃₅—Ph-* p-C₁₇H₃₅—Ph-* p-C₁₇H₃₅—Ph-* Compound 57 S S p-C₁₈H₃₇—Ph-* p-C₁₈H₃₇—Ph-* p-C₁₈H₃₇—Ph-* p-C₁₈H₃₇—Ph-* Compound 58 S S

H

H Compound 59 S S

H

H Compound 60 S S

H

H Compound 61 S S

H

H Compound 62 S S

H

H Compound 63 S S

H

H Compound 64 S S

H

H Compound 65 S S

H

H Compound 66 S S

H

H Compound 67 S S

H

H Compound 68 S S

H

H Compound 69 S S

H

H Compound 70 S S

H

H Compound 71 S S

H

H Compound 72 S S

H

H Compound 73 S S

H

H

TABLE 3 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 74 S S

H

H Compound 75 S S

H

H Compound 76 S S

H

H Compound 77 S S

H

H Compound 78 S S

H

H Compound 79 S S

H

H Compound 80 S S

H

H Compound 81 S S

H

H Compound 82 S S

H

H Compound 83 S S

H

H Compound 84 S S

H

H Compound 85 S S

H

H Compound 86 S S

Compound 87 S S

Compound 88 S S

Compound 89 S S

Compound 90 S S

Compound 91 S S

TABLE 4 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 92  S S

Compound 93  S S

Compound 94  S S

Compound 95  S S

Compound 96  S S

Compound 97  S S

Compound 98  S S

Compound 99  S S

Compound 100 S S

H

H Compound 101 S S

H

H Compound 102 S S

H

H Compound 103 S S

H

H Compound 104 S S

H

H Compound 105 S S

H

H Compound 106 S S

H

H Compound 107 S S

H

H Compound 108 S S

H

H Compound 109 S S

H

H

TABLE 5 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 110 S S

H

H Compound 111 S S

H

H Compound 112 S S

H

H Compound 113 S S

H

H Compound 114 S S

Compound 115 S S

Compound 116 S S

Compound 117 S S

Compound 118 S S

Compound 119 S S

Compound 120 S S

Compound 121 S S

Compound 122 S S

Compound 123 S S

Compound 124 S S

Compound 125 S S

Compound 126 S S

Compound 127 S S

TABLE 6 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 128 S S H C₅H₁₁-* H C₅H₁₁-* Compound 129 S S H C₆H₁₃-* H C₆H₁₃-* Compound 130 S S H C₇H₁₅-* H C₇H₁₅-* Compound 131 S S H C₈H₁₇-* H C₈H₁₇-* Compound 132 S S H C₉H₁₉-* H C₉H₁₉-* Compound 133 S S H C₁₀H₂₁-* H C₁₀H₂₁-* Compound 134 S S H C₁₁H₂₃-* H C₁₁H₂₃-* Compound 135 S S H C₁₂H₂₅-* H C₁₂H₂₅-* Compound 136 S S H C₁₃H₂₇-* H C₁₃H₂₇-* Compound 137 S S H C₁₄H₂₉-* H C₁₄H₂₉-* Compound 138 S S H C₁₅H₃₁-* H C₁₅H₃₁-* Compound 139 S S H C₁₆H₃₃-* H C₁₆H₃₃-* Compound 140 S S H C₁₇H₃₅-* H C₁₇H₃₅-* Compound 141 S S H C₁₈H₃₇-* H C₁₈H₃₇-* Compound 142 S S H p-C₅H₁₁—Ph-* H p-C₅H₁₁—Ph-* Compound 143 S S H p-C₆H₁₃—Ph-* H p-C₆H₁₃—Ph-* Compound 144 S S H p-C₇H₁₅—Ph-* H p-C₇H₁₅—Ph-* Compound 145 S S H p-C₈H₁₇—Ph-* H p-C₈H₁₇—Ph-* Compound 146 S S H p-C₉H₁₉—Ph-* H p-C₉H₁₉—Ph-* Compound 147 S S H p-C₁₀H₂₁—Ph-* H p-C₁₀H₂₁—Ph-* Compound 148 S S H p-C₁₁H₂₃—Ph-* H p-C₁₁H₂₃—Ph-* Compound 149 S S H p-C₁₂H₂₅—Ph-* H p-C₁₂H₂₅—Ph-* Compound 150 S S H p-C₁₃H₂₇—Ph-* H p-C₁₃H₂₇—Ph-* Compound 151 S S H p-C₁₄H₂₉—Ph-* H p-C₁₄H₂₉—Ph-* Compound 152 S S H p-C₁₅H₃₁—Ph-* H p-C₁₅H₃₁—Ph-* Compound 153 S S H p-C₁₆H₃₃—Ph-* H p-C₁₆H₃₃—Ph-* Compound 154 S S H p-C₁₇H₃₅—Ph-* H p-C₁₇H₃₅—Ph-* Compound 155 S S H p-C₁₈H₃₇—Ph-* H p-C₁₈H₃₇—Ph-* Compound 156 S S H

H

Compound 157 S S H

H

Compound 158 S S H

H

Compound 159 S S H

H

Compound 160 S S H

H

Compound 161 S S H

H

Compound 162 S S H

H

Compound 163 S S H

H

TABLE 7 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 164 S S H

H

Compound 165 S S H

H

Compound 166 S S H

H

Compound 167 S S H

H

Compound 168 S S H

H

Compound 169 S S H

H

Compound 170 S S H H C₅H₁₁-* H Compound 171 S S H H C₆H₁₃-* H Compound 172 S S H H C₇H₁₅-* H Compound 173 S S H H C₈H₁₇-* H Compound 174 S S H H C₉H₁₉-* H Compound 175 S S H H C₁₀H₂₁-* H Compound 176 S S H H C₁₁H₂₃-* H Compound 177 S S H H C₁₂H₂₅-* H Compound 178 S S H H C₁₃H₂₇-* H Compound 179 S S H H C₁₄H₂₉-* H Compound 180 S S H H C₁₅H₃₁-* H Compound 181 S S H H C₁₆H₃₃-* H Compound 182 S S H H C₁₇H₃₅-* H Compound 183 S S H H C₁₈H₃₇-* H Compound 184 S S Ph H C₅H₁₁-* H Compound 185 S S Ph H C₆H₁₃-* H Compound 186 S S Ph H C₇H₁₅-* H Compound 187 S S Ph H C₈H₁₇-* H Compound 188 S S Ph H C₉H₁₉-* H Compound 189 S S Ph H C₁₀H₂₁-* H Compound 190 S S Ph H C₁₁H₂₃-* H Compound 191 S S Ph H C₁₂H₂₅-* H Compound 192 S S Ph H C₁₃H₂₇-* H Compound 193 S S Ph H C₁₄H₂₉-* H Compound 194 S S Ph H C₁₅H₃₁-* H Compound 195 S S Ph H C₁₆H₃₃-* H Compound 196 S S Ph H C₁₇H₃₅-* H Compound 197 S S Ph H C₁₈H₃₇-* H Compound 198 S S H H C₅H₁₁-* H Compound 199 S S H H C₆H₁₃-* H

TABLE 8 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 200 S S

H C₇H₁₅-* H Compound 201 S S

H C₈H₁₇-* H Compound 202 S S

H C₉H₁₉-* H Compound 203 S S

H C₁₀H₂₁-* H Compound 204 S S

H C₁₁H₂₃-* H Compound 205 S S

H C₁₂H₂₅-* H Compound 206 S S

H C₁₃H₂₇-* H Compound 207 S S

H C₁₄H₂₉-* H Compound 208 S S

H C₁₅H₃₁-* H Compound 209 S S

H C₁₆H₃₃-* H Compound 210 S S

H C₁₇H₃₅-* H Compound 211 S S

H C₁₈H₃₇-* H Compound 212 S S H H H C₅H₁₁-* Compound 213 S S H H H C₆H₁₃-* Compound 214 S S H H H C₇H₁₅-* Compound 215 S S H H H C₈H₁₇-* Compound 216 S S H H H C₉H₁₉-* Compound 217 S S H H H C₁₀H₂₁-* Compound 218 S S H H H C₁₁H₂₃-* Compound 219 S S H H H C₁₂H₂₅-* Compound 220 S S H H H C₁₃H₂₇-* Compound 221 S S H H H C₁₄H₂₉-* Compound 222 S S H H H C₁₅H₃₁-* Compound 223 S S H H H C₁₆H₃₃-* Compound 224 S S H H H C₁₇H₃₅-* Compound 225 S S H H H C₁₈H₃₇-* Compound 226 S S H H p-C₅H₁₁—Ph-* H Compound 227 S S H H p-C₆H₁₃—Ph-* H Compound 228 S S H H p-C₇H₁₅—Ph-* H Compound 229 S S H H p-C₈H₁₇—Ph-* H Compound 230 S S H H p-C₉H₁₉—Ph-* H

TABLE 9 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 231 S S H H p-C₁₀H₂₁—Ph-* H Compound 232 S S H H p-C₁₁H₂₃—Ph-* H Compound 233 S S H H p-C₁₂H₂₅—Ph-* H Compound 234 S S H H p-C₁₃H₂₇—Ph-* H Compound 235 S S H H p-C₁₄H₂₉—Ph-* H Compound 236 S S H H p-C₁₅H₃₁—Ph-* H Compound 237 S S H H p-C₁₆H₃₃—Ph-* H Compound 238 S S H H p-C₁₇H₃₅—Ph-* H Compound 239 S S H H p-C₁₈H₃₇—Ph-* H Compound 240 S S Ph H p-C₅H₁₁—Ph-* H Compound 241 S S Ph H p-C₆H₁₃—Ph-* H Compound 242 S S Ph H p-C₇H₁₅—Ph-* H Compound 243 S S Ph H p-C₈H₁₇—Ph-* H Compound 244 S S Ph H p-C₉H₁₉—Ph-* H Compound 245 S S Ph H p-C₁₀H₂₁—Ph-* H Compound 246 S S Ph H p-C₁₁H₂₃—Ph-* H Compound 247 S S Ph H p-C₁₂H₂₅—Ph-* H Compound 248 S S Ph H p-C₁₃H₂₇—Ph-* H Compound 249 S S Ph H p-C₁₄H₂₉—Ph-* H Compound 250 S S Ph H p-C₁₅H₃₁—Ph-* H Compound 251 S S Ph H p-C₁₆H₃₃—Ph-* H Compound 252 S S Ph H p-C₁₇H₃₅—Ph-* H Compound 253 S S Ph H p-C₁₈H₃₇—Ph-* H Compound 254 S S

H p-C₅H₁₁—Ph-* H Compound 255 S S

H p-C₆H₁₃—Ph-* H Compound 256 S S

H p-C₇H₁₅—Ph-* H Compound 257 S S

H p-C₈H₁₇—Ph-* H Compound 258 S S

H p-C₉H₁₉—Ph-* H Compound 259 S S

H p-C₁₀H₂₁—Ph-* H Compound 260 S S

H p-C₁₁H₂₃—Ph-* H Compound 261 S S

H p-C₁₂H₂₅—Ph-* H Compound 262 S S

H p-C₁₃H₂₇—Ph-* H Compound 263 S S

H p-C₁₄H₂₉—Ph-* H

TABLE 10 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 264 S S

H p-C₁₅H₃₁—Ph-* H Compound 265 S S

H p-C₁₆H₃₃—Ph-* H Compound 266 S S

H p-C₁₇H₃₅—Ph-* H Compound 267 S S

H p-C₁₈H₃₇—Ph-* H Compound 268 S S H H H p-C₅H₁₁—Ph-* Compound 269 S S H H H p-C₆H₁₃—Ph-* Compound 270 S S H H H p-C₇H₁₅—Ph-* Compound 271 S S H H H p-C₈H₁₇—Ph-* Compound 272 S S H H H p-C₉H₁₉—Ph-* Compound 273 S S H H H p-C₁₀H₂₁—Ph-* Compound 274 S S H H H p-C₁₁H₂₃—Ph-* Compound 275 S S H H H p-C₁₂H₂₅—Ph-* Compound 276 S S H H H p-C₁₃H₂₇—Ph-* Compound 277 S S H H H p-C₁₄H₂₉—Ph-* Compound 278 S S H H H p-C₁₅H₃₁—Ph-* Compound 279 S S H H H p-C₁₆H₃₃—Ph-* Compound 280 S S H H H p-C₁₇H₃₅—Ph-* Compound 281 S S H H H p-C₁₈H₃₇—Ph-* Compound 282 S S H H

H Compound 283 S S H H

H Compound 284 S S H H

H Compound 285 S S H H

H Compound 286 S S H H

H Compound 287 S S H H

H Compound 288 S S H H

H Compound 289 S S H H

H Compound 290 S S H H

H

TABLE 11 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Com- pound 291 S S H H

H Com- pound 292 S S H H

H Com- pound 293 S S H H

H Com- pound 294 S S H H

H Com- pound 295 S S Ph H

H Com- pound 296 S S Ph H

H Com- pound 297 S S Ph H

H Com- pound 298 S S Ph H

H Com- pound 299 S S Ph H

H Com- pound 300 S S Ph H

H Com- pound 301 S S Ph H

H Com- pound 302 S S Ph H

H Com- pound 303 S S Ph H

H Com- pound 304 S S Ph H

H Com- pound 305 S S Ph H

H Com- pound 306 S S Ph H

H Com- pound 307 S S Ph H

H Com- pound 308 S S

H

H

TABLE 12 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 309 S S

H

H Compound 310 S S

H

H Compound 311 S S

H

H Compound 312 S S

H

H Compound 313 S S

H

H Compound 314 S S

H

H Compound 315 S S

H

H Compound 316 S S

H

H Compound 317 S S

H

H Compound 318 S S

H

H Compound 319 S S

H

H Compound 320 S S

H

H Compound 321 S S H H H

Compound 322 S S H H H

Compound 323 S S H H H

Compound 324 S S H H H

Compound 325 S S H H H

Compound 326 S S H H H

TABLE 13 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 327 S S H H H

Compound 328 S S H H H

Compound 329 S S H H H

Compound 330 S S H H H

Compound 331 S S H H H

Compound 332 S S H H H

Compound 333 S S H H H

Compound 334 S S H H

H Compound 335 S S H H

H Compound 336 S S H H

H Compound 337 S S H H

H Compound 338 S S H H

H Compound 339 S S H H

H Compound 340 S S H H

H Compound 341 S S H H

H Compound 342 S S H H

H Compound 343 S S H H

H Compound 344 S S H H

H

TABLE 14 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 345 S S H H

H Compound 346 S S H H

H Compound 347 S S H H

H Compound 348 S S Ph H

H Compound 349 S S Ph H

H Compound 350 S S Ph H

H Compound 351 S S Ph H

H Compound 352 S S Ph H

H Compound 353 S S Ph H

H Compound 354 S S Ph H

H Compound 355 S S Ph H

H Compound 356 S S Ph H

H Compound 357 S S Ph H

H Compound 358 S S Ph H

H Compound 359 S S Ph H

H Compound 360 S S Ph H

H Compound 361 S S Ph H

H Compound 362 S S

H

H

TABLE 15 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 363 S S

H

H Compound 364 S S

H

H Compound 365 S S

H

H Compound 366 S S

H

H Compound 367 S S

H

H Compound 368 S S

H

H Compound 369 S S

H

H Compound 370 S S

H

H Compound 371 S S

H

H Compound 372 S S

H

H Compound 373 S S

H

H Compound 374 S S

H

H Compound 375 S S

H

H Compound 376 S S C₁₀H₂₁—* H p-C₅H₁₁—Ph—* H Compound 377 S S C₁₀H₂₁—* H p-C₆H₁₃—Ph—* H Compound 378 S S C₁₀H₂₁—* H p-C₇H₁₅—Ph—* H Compound 379 S S C₁₀H₂₁—* H p-C₈H₁₇—Ph—* H Compound 380 S S C₁₀H₂₁—* H p-C₉H₁₉—Ph—* H Compound 381 S S C₁₀H₂₁—* H p-C₁₀H₂₁—Ph—* H Compound 382 S S C₁₀H₂₁—* H p-C₁₁H₂₃—Ph—* H Compound 383 S S C₁₀H₂₁—* H p-C₁₂H₂₅—Ph—* H Compound 384 S S C₁₀H₂₁—* H p-C₁₃H₂₇—Ph—* H Compound 385 S S C₁₀H₂₁—* H p-C₁₄H₂₉—Ph—* H Compound 386 S S C₁₀H₂₁—* H p-C₁₅H₃₁—Ph—* H Compound 387 S S C₁₀H₂₁—* H p-C₁₆H₃₃—Ph—* H Compound 388 S S C₁₀H₂₁—* H p-C₁₇H₃₅—Ph—* H Compound 389 S S C₁₀H₂₁—* H p-C₁₈H₃₇—Ph—* H

TABLE 16 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 390 S S C₁₂H₂₅—* H

H Compound 391 S S C₁₂H₂₅—* H

H Compound 392 S S C₁₂H₂₅—* H

H Compound 393 S S C₁₂H₂₅—* H

H Compound 394 S S C₁₂H₂₅—* H

H Compound 395 S S C₁₂H₂₅—* H

H Compound 396 S S C₁₂H₂₅—* H

H Compound 397 S S C₁₂H₂₅—* H

H Compound 398 S S C₁₂H₂₅—* H

H Compound 399 S S C₁₂H₂₅—* H

H Compound 400 S S C₁₂H₂₅—* H

H Compound 401 S S C₁₂H₂₅—* H

H Compound 402 S S C₁₂H₂₅—* H

H Compound 403 S S C₁₂H₂₅—* H

H Compound 404 S S C₅H₁₁—* H H C₁₂H₂₅—* Compound 405 S S C₆H₁₃—* H H C₁₂H₂₅—* Compound 406 S S C₇H₁₅—* H H C₁₂H₂₅—* Compound 407 S S C₈H₁₇—* H H C₁₂H₂₅—* Compound 408 S S C₉H₁₉—* H H C₁₂H₂₅—* Compound 409 S S C₁₀H₂₁—* H H C₁₂H₂₅—* Compound 410 S S C₁₁H₂₃—* H H C₁₂H₂₅—* Compound 411 S S C₁₂H₂₅—* H H C₁₂H₂₅—* Compound 412 S S C₁₃H₂₇—* H H C₁₂H₂₅—* Compound 413 S S C₁₄H₂₉—* H H C₁₂H₂₅—* Compound 414 S S C₁₅H₃₁—* H H C₁₂H₂₅—* Compound 415 S S C₁₆H₃₃—* H H C₁₂H₂₅—* Compound 416 S S C₁₇H₃₅—* H H C₁₂H₂₅—* Compound 417 S S C₁₈H₃₇—* H H C₁₂H₂₅—*

TABLE 17 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 418 S S C₁₀H₂₁—* H H p-C₅H₁₁—Ph—* Compound 419 S S C₁₀H₂₁—* H H p-C₆H₁₃—Ph—* Compound 420 S S C₁₀H₂₁—* H H p-C₇H₁₅—Ph—* Compound 421 S S C₁₀H₂₁—* H H p-C₈H₁₇—Ph—* Compound 422 S S C₁₀H₂₁—* H H p-C₉H₁₉—Ph—* Compound 423 S S C₁₀H₂₁—* H H p-C₁₀H₂₁—Ph—* Compound 424 S S C₁₀H₂₁—* H H p-C₁₁H₂₃—Ph—* Compound 425 S S C₁₀H₂₁—* H H p-C₁₂H₂₅—Ph—* Compound 426 S S C₁₀H₂₁—* H H p-C₁₃H₂₇—Ph—* Compound 427 S S C₁₀H₂₁—* H H p-C₁₄H₂₉—Ph—* Compound 428 S S C₁₀H₂₁—* H H p-C₁₅H₃₁—Ph—* Compound 429 S S C₁₀H₂₁—* H H p-C₁₆H₃₃—Ph—* Compound 430 S S C₁₀H₂₁—* H H p-C₁₇H₃₅—Ph—* Compound 431 S S C₁₀H₂₁—* H H p-C₁₈H₃₇—Ph—* Compound 432 S S H C₁₀H₂₁—* H p-C₅H₁₁—Ph—* Compound 433 S S H C₁₀H₂₁—* H p-C₆H₁₃—Ph—* Compound 434 S S H C₁₀H₂₁—* H p-C₇H₁₅—Ph—* Compound 435 S S H C₁₀H₂₁—* H p-C₈H₁₇—Ph—* Compound 436 S S H C₁₀H₂₁—* H p-C₉H₁₉—Ph—* Compound 437 S S H C₁₀H₂₁—* H p-C₁₀H₂₁—Ph—* Compound 438 S S H C₁₀H₂₁—* H p-C₁₁H₂₃—Ph—* Compound 439 S S H C₁₀H₂₁—* H p-C₁₂H₂₅—Ph—* Compound 440 S S H C₁₀H₂₁—* H p-C₁₃H₂₇—Ph—* Compound 441 S S H C₁₀H₂₁—* H p-C₁₄H₂₉—Ph—* Compound 442 S S H C₁₀H₂₁—* H p-C₁₅H₃₁—Ph—* Compound 443 S S H C₁₀H₂₁—* H p-C₁₆H₃₃—Ph—* Compound 444 S S H C₁₀H₂₁—* H p-C₁₇H₃₅—Ph—* Compound 445 S S H C₁₀H₂₁—* H p-C₁₈H₃₇—Ph—* Compound 446 S S

H

H Compound 447 S S

H

H Compound 448 S S

H

H Compound 449 S S

H

H Compound 450 S S

H

H Compound 451 S S

H

H Compound 452 S S

H

H Compound 453 S S

H

H

TABLE 18 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 454 S S

H

H Compound 455 S S

H

H Compound 456 S S

H

H Compound 457 S S

H

H Compound 458 S S

H

H Compound 459 S S

H

H Compound 460 S S

H

H Compound 461 S S

H

H Compound 462 S S

H

H Compound 463 S S

H

H Compound 464 S S

H

H Compound 465 S S

H

H Compound 466 S S

H

H Compound 467 S S

H

H Compound 468 S S

H

H Compound 469 S S

H

H Compound 470 S S

H

H Compound 471 S S

H

H

TABLE 19 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 472 S S

H

H Compound 473 S S

H

H Compound 474 S S

H

H Compound 475 S S

H

H Compound 476 S S

H

H Compound 477 S S

H

H Compound 478 S S

H

H Compound 479 S S

H

H Compound 480 S S

H

H Compound 481 S S

H

H Compound 482 S S

H

H Compound 483 S S

H

H Compound 484 S S

H

H Compound 485 S S

H

H Compound 486 S S

H

H Compound 487 O O C₅H₁₁—* H C₅H₁₁—* H Compound 488 O O C₆H₁₃—* H C₆H₁₃—* H Compound 489 O O C₇H₁₅—* H C₇H₁₅—* H Compound 490 O O C₈H₁₇—* H C₈H₁₇—* H Compound 491 O O C₉H₁₉—* H C₉H₁₉—* H Compound 492 O O C₁₀H₂₁—* H C₁₀H₂₁—* H Compound 493 O O C₁₁H₂₃—* H C₁₁H₂₃—* H Compound 494 O O C₁₂H₂₅—* H C₁₂H₂₅—* H Compound 495 O O C₁₃H₂₇—* H C₁₃H₂₇—* H Compound 496 O O C₁₄H₂₉—* H C₁₄H₂₉—* H Compound 497 O O C₁₅H₃₁—* H C₁₅H₃₁—* H

TABLE 20 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 498 O O C₁₆H₃₃—* H C₁₆H₃₃—* H Compound 499 O O C₁₇H₃₅—* H C₁₇H₃₅—* H Compound 500 O O C₁₈H₃₇—* H C₁₈H₃₇—* H Compound 501 O O p-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—* H Compound 502 O O p-C₆H₁₃—Ph—* H p-C₆H₁₃—Ph—* H Compound 503 O O p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* H Compound 504 O O p-C₈H₁₇—Ph—* H p-C₈H₁₇—Ph—* H Compound 505 O O p-C₉H₁₉—Ph—* H p-C₉H₁₉—Ph—* H Compound 506 O O p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* H Compound 507 O O p-C₁₁H₂₃—Ph—* H p-C₁₁H₂₃—Ph—* H Compound 508 O O p-C₁₂H₂₅—Ph—* H p-C₁₂H₂₅—Ph—* H Compound 509 O O p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—* H Compound 510 O O p-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* H Compound 511 O O p-C₁₅H₃₁—Ph—* H p-C₁₅H₃₁—Ph—* H Compound 512 O O p-C₁₆H₃₃—Ph—* H p-C₁₆H₃₃—Ph—* H Compound 513 O O p-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* H Compound 514 O O p-C₁₈H₃₇—Ph—* H p-C₁₈H₃₇—Ph—* H Compound 515 O O

H

H Compound 516 O O

H

H Compound 517 O O

H

H Compound 518 O O

H

H Compound 519 O O

H

H Compound 520 O O

H

H Compound 521 O O

H

H Compound 522 O O

H

H Compound 523 O O

H

H Compound 524 O O

H

H Compound 525 O O

H

H Compound 526 O O

H

H

TABLE 21 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 527 O O

H

H Compound 528 O O

H

H Compound 529 S S C₄H 

 OC₄H₅—* H C₄H 

 OC₄H₅—* H Compound 530 S S C₂H₅OC₂H 

 —* H C₂H₅OC₂H 

 —* H Compound 531 S S C 

 H₁₂OC₄H 

 —* H C 

 H₁₂OC₄H 

 —* H Compound 532 S S C₂H₃OC₄H 

 —* H C₂H₃OC₄H 

 —* H Compound 533 S S CH 

 OC₃H₆—* H CH 

 OC₃H₆—* H Compound 534 S S

H

H Compound 535 S S

H

H Compound 536 S S

H

H Compound 537 S S PhC₃H₆—* H PhC₃H₅—* H Compound 538 S S PhOC₃H₆—* H PhOC₃H₅—* H Compound 539 S S

H

H Compound 540 S S

H

H Compound 541 S S

H

H Compound 542 S S

H

H Compound 543 S S

H

H Compound 544 S S 3,7-Dimethyloctyl H 3,7-Dimethyloctyl H

indicates data missing or illegible when filed

TABLE 22 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound S S 3,7-Dimethyloctyl H H H 545 Compound S S 2-Ethylhexyl H 2-Ethylhexyl H 546 Compound 547 S S

H

H Compound 548 S S

H

H Compound 549 S S

H

H Compound 550 S S

H H H Compound 551 S S

H

H Compound 552 S S C₈H₁₁—* H

H Compound 553 S S

H

H Compound 554 S S

H

H Compound 555 S S

H

H Compound 556 S S

H

H Compound 557 S S

H

H Compound 558 S S

H H H Compound 559 S S

H

H Compound 560 S S

H

H Compound 561 S S

H

H Compound 562 S S

H

H

TABLE 23 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 563 S S C₅H₁₁—* H C₅H₁₁—* H Compound 564 S S C₆H₁₃—* H C₆H₁₃—* H Compound 565 S S C₇H₁₅—* H C₇H₁₅—* H Compound 566 S S C₈H₁₇—* H C₈H₁₇—* H Compound 567 S S C₉H₁₉—* H C₉H₁₉—* H Compound 568 S S C₁₀H₂₁—* H C₁₀H₂₁—* H Compound 569 S S C₁₁H₂₃—* H C₁₁H₂₃—* H Compound 570 S S C₁₂H₂₅—* H C₁₂H₂₅—* H Compound 571 S S C₁₃H₂₇—* H C₁₃H₂₇—* H Compound 572 S S C₁₄H₂₉—* H C₁₄H₂₉—* H Compound 573 S S C₁₅H₃₁—* H C₁₅H₃₁—* H Compound 574 S S C₁₆H₃₃—* H C₁₆H₃₃—* H Compound 575 S S C₁₇H₃₅—* H C₁₇H₃₅—* H Compound 576 S S C₁₈H₃₇—* H C₁₈H₃₇—* H Compound 577 S S C₅H₁₁—* C₅H₁₁—* C₅H₁₁—* C₅H₁₁—* Compound 578 S S C₆H₁₃—* C₆H₁₃—* C₆H₁₃—* C₆H₁₃—* Compound 579 S S C₇H₁₅—* C₇H₁₅—* C₇H₁₅—* C₇H₁₅—* Compound 580 S S C₈H₁₇—* C₈H₁₇—* C₈H₁₇—* C₈H₁₇—* Compound 581 S S C₉H₁₉—* C₉H₁₉—* C₉H₁₉—* C₉H₁₉—* Compound 582 S S C₁₀H₂₁—* C₁₀H₂₁—* C₁₀H₂₁—* C₁₀H₂₁—* Compound 583 S S C₁₁H₂₃—* C₁₁H₂₃—* C₁₁H₂₃—* C₁₁H₂₃—* Compound 584 S S C₁₂H₂₅—* C₁₂H₂₅—* C₁₂H₂₅—* C₁₂H₂₅—* Compound 585 S S C₁₃H₂₇—* C₁₃H₂₇—* C₁₃H₂₇—* C₁₃H₂₇—* Compound 586 S S C₁₄H₂₉—* C₁₄H₂₉—* C₁₄H₂₉—* C₁₄H₂₉—* Compound 587 S S C₁₅H₃₁—* C₁₅H₃₁—* C₁₅H₃₁—* C₁₅H₃₁—* Compound 588 S S C₁₆H₃₃—* C₁₆H₃₃—* C₁₆H₃₃—* C₁₆H₃₃—* Compound 589 S S C₁₇H₃₅—* C₁₇H₃₅—* C₁₇H₃₅—* C₁₇H₃₅—* Compound 590 S S C₁₈H₃₇—* C₁₈H₃₇—* C₁₈H₃₇—* C₁₈H₃₇—* Compound 591 S S p-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—* H Compound 592 S S p-C₆H₁₃—Ph—* H p-C₆H₁₃—Ph—* H Compound 593 S S p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* H Compound 594 S S p-C₈H₁₇—Ph—* H p-C₈H₁₇—Ph—* H Compound 595 S S p-C₉H₁₉—Ph—* H p-C₉H₁₉—Ph—* H Compound 596 S S p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* H Compound 597 S S p-C₁₁H₂₃—Ph—* H p-C₁₁H₂₃—Ph—* H Compound 598 S S p-C₁₂H₂₅—Ph—* H p-C₁₂H₂₅—Ph—* H Compound 599 S S p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—* H Compound 600 S S p-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* H Compound 601 S S p-C₁₅H₃₁—Ph—* H p-C₁₅H₃₁—Ph—* H Compound 602 S S p-C₁₆H₃₃—Ph—* H p-C₁₆H₃₃—Ph—* H Compound 603 S S p-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* H Compound 604 S S p-C₁₈H₃₇—Ph—* H p-C₁₈H₃₇—Ph—* H Compound 605 S S p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* Compound 606 S S p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* Compound 607 S S p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* Compound 608 S S p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* Compound 609 S S p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* Compound 610 S S p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* Compound 611 S S p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* Compound 612 S S p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* Compound 613 S S p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—*

TABLE 24 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 614 S S p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* Compound 615 S S p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* Compound 616 S S p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* Compound 617 S S p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* Compound 618 S S p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* Compound 619 S S

H

H Compound 620 S S

H

H Compound 621 S S

H

H Compound 622 S S

H

H Compound 623 S S

H

H Compound 624 S S

H

H Compound 625 S S

H

H Compound 626 S S

H

H Compound 627 S S

H

H Compound 628 S S

H

H Compound 629 S S

H

H Compound 630 S S

H

H Compound 631 S S

H

H Compound 632 S S

H

H Compound 633 S S

Compound 634 S S

Compound 635 S S

TABLE 25 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 636 S S

Compound 637 S S

Compound 638 S S

Compound 639 S S

Compound 640 S S

Compound 641 S S

Compound 642 S S

Compound 643 S S

Compound 644 S S

Compound 645 S S

Compound 646 S S

Compound 647 S S

H

H Compound 648 S S

H

H Compound 649 S S

H

H Compound 650 S S

H

H Compound 651 S S

H

H Compound 652 S S

H

H Compound 653 S S

H

H

TABLE 26 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 654 S S

H

H Compound 655 S S

H

H Compound 656 S S

H

H Compound 657 S S

H

H Compound 658 S S

H

H Compound 659 S S

H

H Compound 660 S S

H

H Compound 661 S S

Compound 662 S S

Compound 663 S S

Compound 664 S S

Compound 665 S S

Compound 666 S S

Compound 667 S S

Compound 668 S S

Compound 669 S S

Compound 670 S S

Compound 671 S S

TABLE 27 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 672 S S

Compound 673 S S

Compound 674 S S

Compound 675 S S H C₅H₁₁—* H C₅H₁₁—* Compound 676 S S H C₆H₁₃—* H C₆H₁₃—* Compound 677 S S H C₇H₁₅—* H C₇H₁₅—* Compound 678 S S H C₈H₁₇—* H C₈H₁₇—* Compound 679 S S H C₉H₁₉—* H C₉H₁₉—* Compound 680 S S H C₁₀H₂₁—* H C₁₀H₂₁—* Compound 681 S S H C₁₁H₂₃—* H C₁₁H₂₃—* Compound 682 S S H C₁₂H₂₅—* H C₁₂H₂₅—* Compound 683 S S H C₁₃H₂₇—* H C₁₃H₂₇—* Compound 684 S S H C₁₄H₂₉—* H C₁₄H₂₉—* Compound 685 S S H C₁₅H₃₁—* H C₁₅H₃₁—* Compound 686 S S H C₁₆H₃₃—* H C₁₆H₃₃—* Compound 687 S S H C₁₇H₃₅—* H C₁₇H₃₅—* Compound 688 S S H C₁₈H₃₇—* H C₁₈H₃₇—* Compound 689 S S H p-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—* Compound 690 S S H p-C₆H₁₃—Ph—* H p-C₆H₁₃—Ph—* Compound 691 S S H p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* Compound 692 S S H p-C₈H₁₇—Ph—* H p-C₈H₁₇—Ph—* Compound 693 S S H p-C₉H₁₉—Ph—* H p-C₉H₁₉—Ph—* Compound 694 S S H p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* Compound 695 S S H p-C₁₁H₂₃—Ph—* H p-C₁₁H₂₃—Ph—* Compound 696 S S H p-C₁₂H₂₅—Ph—* H p-C₁₂H₂₅—Ph—* Compound 697 S S H p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—* Compound 698 S S H p-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* Compound 699 S S H p-C₁₅H₃₁—Ph—* H p-C₁₅H₃₁—Ph—* Compound 700 S S H p-C₁₆H₃₃—Ph—* H p-C₁₆H₃₃—Ph—* Compound 701 S S H p-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* Compound 702 S S H p-C₁₈H₃₇—Ph—* H p-C₁₈H₃₇—Ph—* Compound 703 S S H

H

Compound 704 S S H

H

Compound 705 S S H

H

Compound 706 S S H

H

Compound 707 S S H

H

TABLE 28 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 708 S S H

H

Compound 709 S S H

H

Compound 710 S S H

H

Compound 711 S S H

H

Compound 712 S S H

H

Compound 713 S S H

H

Compound 714 S S H

H

Compound 715 S S H

H

Compound 716 S S H

H

Compound 717 S S H H C₅H₁₁—* H Compound 718 S S H H C₆H₁₃—* H Compound 719 S S H H C₇H₁₅—* H Compound 720 S S H H C₈H₁₇—* H Compound 721 S S H H C₉H₁₉—* H Compound 722 S S H H C₁₀H₂₁—* H Compound 723 S S H H C₁₁H₂₃—* H Compound 724 S S H H C₁₂H₂₅—* H Compound 725 S S H H C₁₃H₂₇—* H Compound 726 S S H H C₁₄H₂₉—* H Compound 727 S S H H C₁₅H₃₁—* H Compound 728 S S H H C₁₆H₃₃—* H Compound 729 S S H H C₁₇H₃₅—* H Compound 730 S S H H C₁₈H₃₇—* H Compound 731 S S Ph H C₅H₁₁—* H Compound 732 S S Ph H C₆H₁₃—* H Compound 733 S S Ph H C₇H₁₅—* H Compound 734 S S Ph H C₈H₁₇—* H Compound 735 S S Ph H C₉H₁₉—* H Compound 736 S S Ph H C₁₀H₂₁—* H Compound 737 S S Ph H C₁₁H₂₃—* H Compound 738 S S Ph H C₁₂H₂₅—* H Compound 739 S S Ph H C₁₃H₂₇—* H Compound 740 S S Ph H C₁₄H₂₉—* H Compound 741 S S Ph H C₁₅H₃₁—* H Compound 742 S S Ph H C₁₆H₃₃—* H Compound 743 S S Ph H C₁₇H₃₅—* H

TABLE 29 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 744 S S Ph H C₁₈H₃₇—* H Compound 745 S S

H C₅H₁₁—* H Compound 746 S S

H C₆H₁₃—* H Compound 747 S S

H C₇H₁₅—* H Compound 748 S S

H C₈H₁₇—* H Compound 749 S S

H C₉H₁₉—* H Compound 750 S S

H C₁₀H₂₁—* H Compound 751 S S

H C₁₁H₂₃—* H Compound 752 S S

H C₁₂H₂₅—* H Compound 753 S S

H C₁₃H₂₇—* H Compound 754 S S

H C₁₄H₂₉—* H Compound 755 S S

H C₁₅H₃₁—* H Compound 756 S S

H C₁₆H₃₃—* H Compound 757 S S

H C₁₇H₃₅—* H Compound 758 S S

H C₁₈H₃₇—* H Compound 759 S S H H H C₅H₁₁—* Compound 760 S S H H H C₆H₁₃—* Compound 761 S S H H H C₇H₁₅—* Compound 762 S S H H H C₈H₁₇—* Compound 763 S S H H H C₉H₁₉—* Compound 764 S S H H H C₁₀H₂₁—* Compound 765 S S H H H C₁₁H₂₃—* Compound 766 S S H H H C₁₂H₂₅—* Compound 767 S S H H H C₁₃H₂₇—* Compound 768 S S H H H C₁₄H₂₉—* Compound 769 S S H H H C₁₅H₃₁—* Compound 770 S S H H H C₁₆H₃₃—* Compound 771 S S H H H C₁₇H₃₅—*

TABLE 30 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 772 S S H H H C₁₈H₃₇-* Compound 773 S S H H p-C₅H₁₁—Ph-* H Compound 774 S S H H p-C₆H₁₃—Ph-* H Compound 775 S S H H p-C₇H₁₅—Ph-* H Compound 776 S S H H p-C₈H₁₇—Ph-* H Compound 777 S S H H p-C₉H₁₉—Ph-* H Compound 778 S S H H p-C₁₀H₂₁—Ph-* H Compound 779 S S H H p-C₁₁H₂₃—Ph-* H Compound 780 S S H H p-C₁₂H₂₅—Ph-* H Compound 781 S S H H p-C₁₃H₂₇—Ph-* H Compound 782 S S H H p-C₁₄H₂₉—Ph-* H Compound 783 S S H H p-C₁₅H₃₁—Ph-* H Compound 784 S S H H p-C₁₆H₃₃—Ph-* H Compound 785 S S H H p-C₁₇H₃₅—Ph-* H Compound 786 S S H H p-C₁₈H₃₇—Ph-* H Compound 787 S S Ph H p-C₅H₁₁—Ph-* H Compound 788 S S Ph H p-C₆H₁₃—Ph-* H Compound 789 S S Ph H p-C₇H₁₅—Ph-* H Compound 790 S S Ph H p-C₈H₁₇—Ph-* H Compound 791 S S Ph H p-C₉H₁₉—Ph-* H Compound 792 S S Ph H p-C₁₀H₂₁—Ph-* H Compound 793 S S Ph H p-C₁₁H₂₃—Ph-* H Compound 794 S S Ph H p-C₁₂H₂₅—Ph-* H Compound 795 S S Ph H p-C₁₃H₂₇—Ph-* H Compound 796 S S Ph H p-C₁₄H₂₉—Ph-* H Compound 797 S S Ph H p-C₁₅H₃₁—Ph-* H Compound 798 S S Ph H p-C₁₆H₃₃—Ph-* H Compound 799 S S Ph H p-C₁₇H₃₅—Ph-* H Compound 800 S S Ph H p-C₁₈H₃₇—Ph-* H Compound 801 S S

H p-C₅H₁₁—Ph-* H Compound 802 S S

H p-C₆H₁₃—Ph-* H Compound 803 S S

H p-C₇H₁₅—Ph-* H Compound 804 S S

H p-C₈H₁₇—Ph-* H Compound 805 S S

H p-C₉H₁₉—Ph-* H Compound 806 S S

H p-C₁₀H₂₁—Ph-* H Compound 807 S S

H p-C₁₁H₂₃—Ph-* H

TABLE 31 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 808 S S

H p-C₁₂H₂₅—Ph-* H Compound 809 S S

H p-C₁₃H₂₇—Ph-* H Compound 810 S S

H p-C₁₄H₂₉—Ph-* H Compound 811 S S

H p-C₁₅H₃₁—Ph-* H Compound 812 S S

H p-C₁₆H₃₃—Ph-* H Compound 813 S S

H p-C₁₇H₃₅—Ph-* H Compound 814 S S

H p-C₁₈H₃₇—Ph-* H Compound 815 S S H H H p-C₅H₁₁—Ph-* Compound 816 S S H H H p-C₆H₁₃—Ph-* Compound 817 S S H H H p-C₇H₁₅—Ph-* Compound 818 S S H H H p-C₈H₁₇—Ph-* Compound 819 S S H H H p-C₉H₁₉—Ph-* Compound 820 S S H H H p-C₁₀H₂₁—Ph-* Compound 821 S S H H H p-C₁₁H₂₃—Ph-* Compound 822 S S H H H p-C₁₂H₂₅—Ph-* Compound 823 S S H H H p-C₁₃H₂₇—Ph-* Compound 824 S S H H H p-C₁₄H₂₉—Ph-* Compound 825 S S H H H p-C₁₅H₃₁—Ph-* Compound 826 S S H H H p-C₁₆H₃₃—Ph-* Compound 827 S S H H H p-C₁₇H₃₅—Ph-* Compound 828 S S H H H p-C₁₈H₃₇—Ph-* Compound 829 S S H H

H Compound 830 S S H H

H Compound 831 S S H H

H Compound 832 S S H H

H Compound 833 S S H H

H Compound 834 S S H H

H

TABLE 32 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 835 S S H H

H Compound 836 S S H H

H Compound 837 S S H H

H Compound 838 S S H H

H Compound 839 S S H H

H Compound 840 S S H H

H Compound 841 S S H H

H Compound 842 S S Ph H

H Compound 843 S S Ph H

H Compound 844 S S Ph H

H Compound 845 S S Ph H

H Compound 846 S S Ph H

H Compound 847 S S Ph H

H Compound 848 S S Ph H

H Compound 849 S S Ph H

H Compound 850 S S Ph H

H Compound 851 S S Ph H

H Compound 852 S S Ph H

H

TABLE 33 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 853 S S Ph H

H Compound 854 S S Ph H

H Compound 855 S S

H

H Compound 856 S S

H

H Compound 857 S S

H

H Compound 858 S S

H

H Compound 859 S S

H

H Compound 860 S S

H

H Compound 861 S S

H

H Compound 862 S S

H

H Compound 863 S S

H

H Compound 864 S S

H

H Compound 865 S S

H

H Compound 866 S S

H

H Compound 867 S S

H

H Compound 868 S S H H H

Compound 869 S S H H H

Compound 870 S S H H H

TABLE 34 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 871 S S H H H

Compound 872 S S H H H

Compound 873 S S H H H

Compound 874 S S H H H

Compound 875 S S H H H

Compound 876 S S H H H

Compound 877 S S H H H

Compound 878 S S H H H

Compound 879 S S H H H

Compound 880 S S H H H

Compound 881 S S H H

H Compound 882 S S H H

H Compound 883 S S H H

H Compound 884 S S H H

H Compound 885 S S H H

H Compound 886 S S H H

H Compound 887 S S H H

H Compound 888 S S H H

H

TABLE 35 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 889 S S H H

H Compound 890 S S H H

H Compound 891 S S H H

H Compound 892 S S H H

H Compound 893 S S H H

H Compound 894 S S H H

H Compound 895 S S Ph H

H Compound 896 S S Ph H

H Compound 897 S S Ph H

H Compound 898 S S Ph H

H Compound 899 S S Ph H

H Compound 900 S S Ph H

H Compound 901 S S Ph H

H Compound 902 S S Ph H

H Compound 903 S S Ph H

H Compound 904 S S Ph H

H Compound 905 S S Ph H

H Compound 906 S S Ph H

H

TABLE 36 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 907 S S Ph H

H Compound 908 S S Ph H

H Compound 909 S S

H

H Compound 910 S S

H

H Compound 911 S S

H

H Compound 912 S S

H

H Compound 913 S S

H

H Compound 914 S S

H

H Compound 915 S S

H

H Compound 916 S S

H

H Compound 917 S S

H

H Compound 918 S S

H

H Compound 919 S S

H

H Compound 920 S S

H

H Compound 921 S S

H

H Compound 922 S S

H

H Compound 923 S S C₁₀H₂₁-* H p-C₅H₁₁—Ph-* H Compound 924 S S C₁₀H₂₁-* H p-C₆H₁₃—Ph-* H Compound 925 S S C₁₀H₂₁-* H p-C₇H₁₅—Ph-* H Compound 926 S S C₁₀H₂₁-* H p-C₈H₁₇—Ph-* H Compound 927 S S C₁₀H₂₁-* H p-C₉H₁₉—Ph-* H Compound 928 S S C₁₀H₂₁-* H p-C₁₀H₂₁—Ph-* H Compound 929 S S C₁₀H₂₁-* H p-C₁₁H₂₃—Ph-* H Compound 930 S S C₁₀H₂₁-* H p-C₁₂H₂₅—Ph-* H

TABLE 37 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound S S C₁₀H₂₁-* H p-C₁₃H₂₇—Ph-* H 931 Compound S S C₁₀H₂₁-* H p-C₁₄H₂₉—Ph-* H 932 Compound S S C₁₀H₂₁-* H p-C₁₅H₃₁—Ph-* H 933 Compound S S C₁₀H₂₁-* H p-C₁₆H₃₃—Ph-* H 934 Compound S S C₁₀H₂₁-* H p-C₁₇H₃₅—Ph-* H 935 Compound S S C₁₀H₂₁-* H p-C₁₈H₃₇—Ph-* H 936 Compound 937 S S C₁₂H₂₅-* H

H Compound 938 S S C₁₂H₂₅-* H

H Compound 939 S S C₁₂H₂₅-* H

H Compound 940 S S C₁₂H₂₅-* H

H Compound 941 S S C₁₂H₂₅-* H

H Compound 942 S S C₁₂H₂₅-* H

H Compound 943 S S C₁₂H₂₅-* H

H Compound 944 S S C₁₂H₂₅-* H

H Compound 945 S S C₁₂H₂₅-* H

H Compound 946 S S C₁₂H₂₅-* H

H Compound 947 S S C₁₂H₂₅-* H

H Compound 948 S S C₁₂H₂₅-* H

H Compound 949 S S C₁₂H₂₅-* H

H Compound 950 S S C₁₂H₂₅-* H

H Compound S S C₅H₁₁-* H H C₁₂H₂₅-* 951 Compound S S C₆H₁₃-* H H C₁₂H₂₅-* 952 Compound S S C₇H₁₅-* H H C₁₂H₂₅-* 953 Compound S S C₈H₁₇-* H H C₁₂H₂₅-* 954 Compound S S C₉H₁₉-* H H C₁₂H₂₅-* 955 Compound S S C₁₀H₂₁-* H H C₁₂H₂₅-* 956 Compound S S C₁₁H₂₃-* H H C₁₂H₂₅-* 957 Compound S S C₁₂H₂₅-* H H C₁₂H₂₅-* 958

TABLE 38 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 959 S S C 

 H 

 -* H H C 

 H 

 -* Compound 960 S S C 

 H 

 -* H H C 

 H 

 -* Compound 961 S S C 

 H 

 -* H H C 

 H 

 -* Compound 962 S S C 

 H 

 -* H H C 

 H 

 -* Compound 963 S S C 

 H 

 -* H H C 

 H 

 -* Compound 964 S S C 

 H 

 -* H H C 

 H 

 -* Compound 965 S S C 

 H 

 -* H H p-C₅H₁₁—Ph-* Compound 966 S S C 

 H 

 -* H H p-C₆H₁₃—Ph-* Compound 967 S S C 

 H 

 -* H H p-C₇H₁₅—Ph-* Compound 968 S S C 

 H 

 -* H H p-C₈H₁₇—Ph-* Compound 969 S S C 

 H 

 -* H H p-C₉H₁₉—Ph-* Compound 970 S S C 

 H 

 -* H H p-C₁₀H₂₁—Ph-* Compound 971 S S C 

 H 

 -* H H p-C₁₁H₂₃—Ph-* Compound 972 S S C 

 H 

 -* H H p-C₁₂H₂₅—Ph-* Compound 973 S S C 

 H 

 -* H H p-C₁₃H₂₇—Ph-* Compound 974 S S C 

 H 

 -* H H p-C₁₄H₂₉—Ph-* Compound 975 S S C 

 H 

 -* H H p-C₁₅H₃₁—Ph-* Compound 976 S S C 

 H 

 -* H H p-C₁₆H₃₃—Ph-* Compound 977 S S C 

 H 

 -* H H p-C₁₇H₃₅—Ph-* Compound 978 S S C 

 H 

 -* H H p-C₁₈H₃₇—Ph-* Compound 979 S S H C 

 H 

 -* H p-C₅H₁₁—Ph-* Compound 980 S S H C 

 H 

 -* H p-C₆H₁₃—Ph-* Compound 981 S S H C 

 H 

 -* H p-C₇H₁₅—Ph-* Compound 982 S S H C 

 H 

 -* H p-C₈H₁₇—Ph-* Compound 983 S S H C 

 H 

 -* H p-C₉H₁₉—Ph-* Compound 984 S S H C 

 H 

 -* H p-C₁₀H₂₁—Ph-* Compound 985 S S H C 

 H 

 -* H p-C₁₁H₂₃—Ph-* Compound 986 S S H C 

 H 

 -* H p-C₁₂H₂₅—Ph-* Compound 987 S S H C 

 H 

 -* H p-C₁₃H₂₇—Ph-* Compound 988 S S H C 

 H 

 -* H p-C₁₄H₂₉—Ph-* Compound 989 S S H C 

 H 

 -* H p-C₁₅H₃₁—Ph-* Compound 990 S S H C 

 H 

 -* H p-C₁₆H₃₃—Ph-* Compound 991 S S H C 

 H 

 -* H p-C₁₇H₃₅—Ph-* Compound 992 S S H C 

 H 

 -* H p-C₁₈H₃₇—Ph-* Compound 993 S S

H

H Compound 994 S S

H

H Compound 995 S S

H

H Compound 996 S S

H

H Compound 997 S S

H

H Compound 998 S S

H

H

indicates data missing or illegible when filed

TABLE 39 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 999  S S

H

H Compound 1000 S S

H

H Compound 1001 S S

H

H Compound 1002 S S

H

H Compound 1003 S S

H

H Compound 1004 S S

H

H Compound 1005 S S

H

H Compound 1006 S S

H

H Compound 1007 S S

H

H Compound 1008 S S

H

H Compound 1009 S S

H

H Compound 1010 S S

H

H Compound 1011 S S

H

H Compound 1012 S S

H

H Compound 1013 S S

H

H Compound 1014 S S

H

H Compound 1015 S S

H

H Compound 1016 S S

H

H

TABLE 40 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 1017 S S

H

H Compound 1018 S S

H

H Compound 1019 S S

H

H Compound 1020 S S

H

H Compound 1021 S S

H

H Compound 1022 S S

H

H Compound 1023 S S

H

H Compound 1024 S S

H

H Compound 1025 S S

H

H Compound 1026 S S

H

H Compound 1027 S S

H

H Compound 1028 S S

H

H Compound 1029 S S

H

H Compound 1030 S S

H

H Compound 1031 S S

H

H Compound 1032 S S

H

H Compound 1033 S S

H

H Compound 1034 O O C₅H₁₁-* H C₅H₁₁-* H Compound 1035 O O C₆H₁₃-* H C₆H₁₃-* H Compound 1036 O O C₇H₁₅-* H C₇H₁₅-* H Compound 1037 O O C₈H₁₇-* H C₈H₁₇-* H Compound 1038 O O C₉H₁₉-* H C₉H₁₉-* H

TABLE 41 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 1039 O O C₁₀H₂₁-* H C₁₀H₂₁-* H Compound 1040 O O C₁₁H₂₃-* H C₁₁H₂₃-* H Compound 1041 O O C₁₂H₂₅-* H C₁₂H₂₅-* H Compound 1042 O O C₁₃H₂₇-* H C₁₃H₂₇-* H Compound 1043 O O C₁₄H₂₉-* H C₁₄H₂₉-* H Compound 1044 O O C₁₅H₃₁-* H C₁₅H₃₁-* H Compound 1045 O O C₁₆H₃₃-* H C₁₆H₃₃-* H Compound 1046 O O C₁₇H₃₅-* H C₁₇H₃₅-* H Compound 1047 O O C₁₈H₃₇-* H C₁₈H₃₇-* H Compound 1048 O O p-C₅H₁₁—Ph-* H p-C₅H₁₁—Ph-* H Compound 1049 O O p-C₆H₁₃—Ph-* H p-C₆H₁₃—Ph-* H Compound 1050 O O p-C₇H₁₅—Ph-* H p-C₇H₁₅—Ph-* H Compound 1051 O O p-C₈H₁₇—Ph-* H p-C₈H₁₇—Ph-* H Compound 1052 O O p-C₉H₁₉—Ph-* H p-C₉H₁₉—Ph-* H Compound 1053 O O p-C₁₀H₂₁—Ph-* H p-C₁₀H₂₁—Ph-* H Compound 1054 O O p-C₁₁H₂₃—Ph-* H p-C₁₁H₂₃—Ph-* H Compound 1055 O O p-C₁₂H₂₅—Ph-* H p-C₁₂H₂₅—Ph-* H Compound 1056 O O p-C₁₃H₂₇—Ph-* H p-C₁₃H₂₇—Ph-* H Compound 1057 O O p-C₁₄H₂₉—Ph-* H p-C₁₄H₂₉—Ph-* H Compound 1058 O O p-C₁₅H₃₁—Ph-* H p-C₁₅H₃₁—Ph-* H Compound 1059 O O p-C₁₆H₃₃—Ph-* H p-C₁₆H₃₃—Ph-* H Compound 1060 O O p-C₁₇H₃₅—Ph-* H p-C₁₇H₃₅—Ph-* H Compound 1061 O O p-C₁₈H₃₇—Ph-* H p-C₁₈H₃₇—Ph-* H Compound 1062 O O

H

H Compound 1063 O O

H

H Compound 1064 O O

H

H Compound 1065 O O

H

H Compound 1066 O O

H

H Compound 1067 O O

H

H Compound 1068 O O

H

H Compound 1069 O O

H

H Compound 1070 O O

H

H Compound 1071 O O

H

H

TABLE 42 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 1072 O O

H

H Compound 1073 O O

H

H Compound 1074 O O

H

H Compound 1075 O O

H

H Compound 1076 S S C 

 H 

 OC 

 H 

 -* H C 

 H 

 OC 

 H 

 -* H Compound 1077 S S C 

 H 

 OC 

 H 

 -* H C 

 H 

 OC 

 H 

 -* H Compound 1078 S S C 

 H 

 OC 

 H 

 -* H C 

 H 

 OC 

 H 

 -* H Compound 1079 S S C 

 H 

 OC 

 H 

 -* H C 

 H 

 OC 

 H 

 -* H Compound 1080 S S CH 

 OC 

 H 

 -* H CH 

 OC 

 H 

 -* H Compound 1081 S S

H

H Compound 1082 S S

H

H Compound 1083 S S

H

H Compound 1084 S S PhO 

 H 

 -* H PhO 

 H 

 -* H Compound 1085 S S PhOC 

 H 

 -* H PhOC 

 H 

 -* H Compound 1086 S S

H

H Compound 1087 S S

H

H Compound 1088 S S

H

H Compound 1089 S S

H

H Compound 1090 S S

H

H Compound 1091 S S 3,7-Dimethyloctyl H 3,7-Dimethyloctyl H Compound 1092 S S 3,7-Dimethyloctyl H H H Compound 1093 S S 2-Ethylhexyl H 2-Ethylhexyl H Compound 1094 S S

H

H Compound 1095 S S

H

H

indicates data missing or illegible when filed

TABLE 43 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 1096 S S

H

H Compound 1097 S S

H H H Compound 1098 S S

H

H Compound 1099 S S C₅H₁₁-* H

H Compound 1100 S S

H

H Compound 1101 S S

H

H Compound 1102 S S

H

H Compound 1103 S S

H

H Compound 1104 S S

H

H Compound 1105 S S

H H H Compound 1106 S S

H

H Compound 1107 S S

H

H Compound 1108 S S

H

H Compound 1109 S S

H

H

TABLE 44 X^(c1) X^(c2) R^(c11) R^(c21) Compound S S C₅H₁₁-* C₅H₁₁-* 1110 Compound S S C₆H₁₃-* C₆H₁₃-* 1111 Compound S S C₇H₁₅-* C₇H₁₅-* 1112 Compound S S C₈H₁₇-* C₈H₁₇-* 1113 Compound S S C₉H₁₉-* C₉H₁₉-* 1114 Compound S S C₁₀H₂₁-* C₁₀H₂₁-* 1115 Compound S S C₁₁H₂₃-* C₁₁H₂₃-* 1116 Compound S S C₁₂H₂₅-* C₁₂H₂₅-* 1117 Compound S S C₁₃H₂₇-* C₁₃H₂₇-* 1118 Compound S S C₁₄H₂₉-* C₁₄H₂₉-* 1119 Compound S S C₁₅H₃₁-* C₁₅H₃₁-* 1120 Compound S S C₁₆H₃₃-* C₁₆H₃₃-* 1121 Compound S S C₁₇H₃₅-* C₁₇H₃₅-* 1122 Compound S S C₁₈H₃₇-* C₁₈H₃₇-* 1123 Compound S S p-C₅H₁₁—Ph-* p-C₅H₁₁—Ph-* 1124 Compound S S p-C₆H₁₃—Ph-* p-C₆H₁₃—Ph-* 1125 Compound S S p-C₇H₁₅—Ph-* p-C₇H₁₅—Ph-* 1126 Compound S S p-C₈H₁₇—Ph-* p-C₈H₁₇—Ph-* 1127 Compound S S p-C₉H₁₉—Ph-* p-C₉H₁₉—Ph-* 1128 Compound S S p-C₁₀H₂₁—Ph-* p-C₁₀H₂₁—Ph-* 1129 Compound S S p-C₁₁H₂₃—Ph-* p-C₁₁H₂₃—Ph-* 1130 Compound S S p-C₁₂H₂₅—Ph-* p-C₁₂H₂₅—Ph-* 1131 Compound S S p-C₁₃H₂₇—Ph-* p-C₁₃H₂₇—Ph-* 1132 Compound S S p-C₁₄H₂₉—Ph-* p-C₁₄H₂₉—Ph-* 1133 Compound S S p-C₁₅H₃₁—Ph-* p-C₁₅H₃₁—Ph-* 1134 Compound S S p-C₁₆H₃₃—Ph-* p-C₁₆H₃₃—Ph-* 1135 Compound S S p-C₁₇H₃₅—Ph-* p-C₁₇H₃₅—Ph-* 1136 Compound S S p-C₁₈H₃₇—Ph-* p-C₁₈H₃₇—Ph-* 1137 Compound 1138 S S

Compound 1139 S S

Compound 1140 S S

Compound 1141 S S

Compound 1142 S S

Compound 1143 S S

Compound 1144 S S

Compound 1145 S S

TABLE 45 x^(c1) X^(c2) R^(c11) R^(c21) Com- pound 1146 S S

Com- pound 1147 S S

Com- pound 1148 S S

Com- pound 1149 S S

Com- pound 1150 S S

Com- pound 1151 S S

Com- pound 1152 S S

Com- pound 1153 S S

Com- pound 1154 S S

Com- pound 1155 S S

Com- pound 1156 S S

Com- pound 1157 S S

Com- pound 1158 S S

Com- pound 1159 S S

Com- pound 1160 S S

Com- pound 1161 S S

Com- pound 1162 S S

Com- pound 1163 S S

TABLE 46 X^(c1) X^(c2) R^(c11) R^(c21) Com- pound 1164 S S

Com- pound 1165 S S

Com- S S H C₅H₁₁—* pound 1166 Com- S S H C₆H₁₃—* pound 1167 Com- S S H C₇H₁₅—* pound 1168 Com- S S H C₈H₁₇—* pound 1169 Com- S S H C₉H₁₉—* pound 1170 Com- S S H C₁₀H₂₁—* pound 1171 Com- S S H C₁₁H₂₃—* pound 1172 Com- S S H C₁₂H₂₅—* pound 1173 Com- S S H C₁₃H₂₇—* pound 1174 Com- S S H C₁₄H₂₉—* pound 1175 Com- S S H C₁₅H₃₁—* pound 1176 Com- S S H C₁₆H₃₃—* pound 1177 Com- S S H C₁₇H₃₅—* pound 1178 Com- S S H C₁₈H₃₇—* pound 1179 Com- S S Ph C₅H₁₁—* pound 1180 Com- S S Ph C₆H₁₃—* pound 1181 Com- S S Ph C₇H₁₅—* pound 1182 Com- S S Ph C₈H₁₇—* pound 1183 Com- S S Ph C₉H₁₉—* pound 1184 Com- S S Ph C₁₀H₂₁—* pound 1185 Com- S S Ph C₁₁H₂₃—* pound 1186 Com- S S Ph C₁₂H₂₅—* pound 1187 Com- S S Ph C₁₃H₂₇—* pound 1188 Com- S S Ph C₁₄H₂₉—* pound 1189 Com- S S Ph C₁₅H₃₁—* pound 1190 Com- S S Ph C₁₆H₃₃—* pound 1191 Com- S S Ph C₁₇H₃₅—* pound 1192 Com- S S Ph C₁₈H₃₇—* pound 1193 Com- pound 1194 S S

C₅H₁₁—* Com- pound 1195 S S

C₆H₁₃—* Com- pound 1196 S S

C₇H₁₅—* Com- pound 1197 S S

C₈H₁₇—* Com- pound 1198 S S

C₉H₁₉—* Com- pound 1199 S S

C₁₀C₂₁—*

TABLE 47 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1200 S S

C₁₁C₂₃—* Compound 1201 S S

C₁₂C₂₅—* Compound 1202 S S

C₁₃C₂₇—* Compound 1203 S S

C₁₄C₂₉—* Compound 1204 S S

C₁₅C₃₁—* Compound 1205 S S

C₁₆C₃₃—* Compound 1206 S S

C₁₇C₃₅—* Compound 1207 S S

C₁₈C₃₇—* Compound 1208 S S H p-C₅H₁₁—Ph—* Compound 1209 S S H p-C₆H₁₃—Ph—* Compound 1210 S S H p-C₇H₁₅—Ph—* Compound 1211 S S H p-C₈H₁₇—Ph—* Compound 1212 S S H p-C₉H₁₉—Ph—* Compound 1213 S S H p-C₁₀H₂₁—Ph—* Compound 1214 S S H p-C₁₁H₂₃—Ph—* Compound 1215 S S H p-C₁₂H₂₅—Ph—* Compound 1216 S S H p-C₁₃H₂₇—Ph—* Compound 1217 S S H p-C₁₄H₂₉—Ph—* Compound 1218 S S H p-C₁₅H₃₁—Ph—* Compound 1219 S S H p-C₁₆H₃₃—Ph—* Compound 1220 S S H p-C₁₇H₃₅—Ph—* Compound 1221 S S H p-C₁₈H₃₇—Ph—* Compound 1222 S S Ph p-C₅H₁₁—Ph—* Compound 1223 S S Ph p-C₆H₁₃—Ph—* Compound 1224 S S Ph p-C₇H₁₅—Ph—* Compound 1225 S S Ph p-C₈H₁₇—Ph—* Compound 1226 S S Ph p-C₉H₁₉—Ph—* Compound 1227 S S Ph p-C₁₀H₂₁—Ph—* Compound 1228 S S Ph p-C₁₁H₂₃—Ph—* Compound 1229 S S Ph p-C₁₂H₂₅—Ph—* Compound 1230 S S Ph p-C₁₃H₂₇—Ph—* Compound 1231 S S Ph p-C₁₄H₂₉—Ph—* Compound 1232 S S Ph p-C₁₅H₃₁—Ph—* Compound 1233 S S Ph p-C₁₆H₃₃—Ph—* Compound 1234 S S Ph p-C₁₇H₃₅—Ph—* Compound 1235 S S Ph p-C₁₈H₃₇—Ph—*

TABLE 48 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1236 S S

p-C₅H₁₁—Ph—* Compound 1237 S S

p-C₆H₁₃—Ph—* Compound 1238 S S

p-C₇H₁₅—Ph—* Compound 1239 S S

p-C₈H₁₇—Ph—* Compound 1240 S S

p-C₉H₁₉—Ph—* Compound 1241 S S

p-C₁₀H₂₁—Ph—* Compound 1242 S S

p-C₁₁H₂₃—Ph—* Compound 1243 S S

p-C₁₂H₂₅—Ph—* Compound 1244 S S

p-C₁₃H₂₇—Ph—* Compound 1245 S S

p-C₁₄H₂₉—Ph—* Compound 1246 S S

p-C₁₅H₃₁—Ph—* Compound 1247 S S

p-C₁₆H₃₃—Ph—* Compound 1248 S S

p-C₁₇H₃₅—Ph—* Compound 1249 S S

p-C₁₈H₃₇—Ph—* Compound 1250 S S H

Compound 1251 S S H

Compound 1252 S S H

Compound 1253 S S H

TABLE 49 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1254 S S H

Compound 1255 S S H

Compound 1256 S S H

Compound 1257 S S H

Compound 1258 S S H

Compound 1259 S S H

Compound 1260 S S H

Compound 1261 S S H

Compound 1262 S S H

Compound 1263 S S Ph

Compound 1264 S S Ph

Compound 1265 S S Ph

Compound 1266 S S Ph

Compound 1267 S S Ph

Compound 1268 S S Ph

Compound 1269 S S Ph

Compound 1270 S S Ph

Compound 1271 S S Ph

TABLE 50 X^(c1) X^(c2) R^(c11) R^(c21) Com- pound 1272 S S Ph

Com- pound 1273 S S Ph

Com- pound 1274 S S Ph

Com- pound 1275 S S Ph

Com- pound 1276 S S

Com- pound 1277 S S

Com- pound 1278 S S

Com- pound 1279 S S

Com- pound 1280 S S

Com- pound 1281 S S

Com- pound 1282 S S

Com- pound 1283 S S

Com- pound 1284 S S

Com- pound 1285 S S

Com- pound 1286 S S

Com- pound 1287 S S

Com- pound 1288 S S

Com- pound 1289 S S H

TABLE 51 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1290 S S H

Compound 1291 S S H

Compound 1292 S S H

Compound 1293 S S H

Compound 1294 S S H

Compound 1295 S S H

Compound 1296 S S H

Compound 1297 S S H

Compound 1298 S S H

Compound 1299 S S H

Compound 1300 S S H

Compound 1301 S S H

Compound 1302 S S H

Compound 1303 S S Ph

Compound 1304 S S Ph

Compound 1305 S S Ph

Compound 1306 S S Ph

Compound 1307 S S Ph

TABLE 52 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1308 S S Ph

Compound 1309 S S Ph

Compound 1310 S S Ph

Compound 1311 S S Ph

Compound 1312 S S Ph

Compound 1313 S S Ph

Compound 1314 S S Ph

Compound 1315 S S Ph

Compound 1316 S S Ph

Compound 1317 S S

Compound 1318 S S

Compound 1319 S S

Compound 1320 S S

Compound 1321 S S

Compound 1322 S S

Compound 1323 S S

Compound 1324 S S

Compound 1325 S S

TABLE 53 X^(c1) X^(c2) R^(c11) R^(c21) Com- pound 1326 S S

Com- pound 1327 S S

Com- pound 1328 S S

Com- pound 1329 S S

Com- pound 1330 S S

Com- S S C₁₀H₂₁—* p-C₅H₁₁—Ph—* pound 1331 Com- S S C₁₀H₂₁—* p-C₆H₁₃—Ph—* pound 1332 Com- S S C₁₀H₂₁—* p-C₇H₁₅—Ph—* pound 1333 Com- S S C₁₀H₂₁—* p-C₈H₁₇—Ph—* pound 1334 Com- S S C₁₀H₂₁—* p-C₉H₁₉—Ph—* pound 1335 Com- S S C₁₀H₂₁—* p-C₁₀H₂₁—Ph—* pound 1336 Com- S S C₁₀H₂₁—* p-C₁₁H₂₃—Ph—* pound 1337 Com- S S C₁₀H₂₁—* p-C₁₂H₂₅—Ph—* pound 1338 Com- S S C₁₀H₂₁—* p-C₁₃H₂₇—Ph—* pound 1339 Com- S S C₁₀H₂₁—* p-C₁₄H₂₉—Ph—* pound 1340 Com- S S C₁₀H₂₁—* p-C₁₅H₃₁—Ph—* pound 1341 Com- S S C₁₀H₂₁—* p-C₁₆H₃₃—Ph—* pound 1342 Com- S S C₁₀H₂₁—* p-C₁₇H₃₅—Ph—* pound 1343 Com- S S C₁₀H₂₁—* p-C₁₈H₃₇—Ph—* pound 1344 Com- pound 1345 S S C₁₂H₂₅—*

Com- pound 1346 S S C₁₂H₂₅—*

Com- pound 1347 S S C₁₂H₂₅—*

Com- pound 1348 S S C₁₂H₂₅—*

Com- pound 1349 S S C₁₂H₂₅—*

Com- pound 1350 S S C₁₂H₂₅—*

Com- pound 1351 S S C₁₂H₂₅—*

Com- pound 1352 S S C₁₂H₂₅—*

TABLE 54 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1353 S S C₁₂H₂₅—*

Compound 1354 S S C₁₂H₂₅—*

Compound 1355 S S C₁₂H₂₅—*

Compound 1356 S S C₁₂H₂₅—*

Compound 1357 S S C₁₂H₂₅—*

Compound 1358 S S C₁₂H₂₅—*

Compound 1359 S S

Compound 1360 S S

Compound 1361 S S

Compound 1362 S S

Compound 1363 S S

Compound 1364 S S

Compound 1365 S S

Compound 1366 S S

Compound 1367 S S

Compound 1368 S S

Compound 1369 S S

Compound 1370 S S

TABLE 55 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1371 S S

Compound 1372 S S

Compound 1373 S S

Compound 1374 S S

Compound 1375 S S

Compound 1376 S S

Compound 1377 S S

Compound 1378 S S

Compound 1379 S S

Compound 1380 S S

Compound 1381 S S

Compound 1382 S S

Compound 1383 S S

Compound 1384 S S

Compound 1385 S S

Compound 1386 S S

Compound 1387 S S

Compound 1388 S S

TABLE 56 X^(c1) X^(c2) X^(c11) X^(c21) Compound 1389 S S

Compound 1390 S S

Compound 1391 S S

Compound 1392 S S

Compound 1393 S S

Compound 1394 S S

Compound 1395 S S

Compound 1396 S S

Compound 1397 S S

Compound 1398 S S

Compound 1399 S S

Compound 1400 O O C₅H₁₁—* C₅H₁₁—* Compound 1401 O O C₆H₁₃—* C₆H₁₃—* Compound 1402 O O C₇H₁₅—* C₇H₁₅—* Compound 1403 O O C₈H₁₇—* C₈H₁₇—* Compound 1404 O O C₉H₁₉—* C₉H₁₉—* Compound 1405 O O C₁₀H₂₁—* C₁₀H₂₁—* Compound 1406 O O C₁₁H₂₃—* C₁₁H₂₃—* Compound 1407 O O C₁₂H₂₅—* C₁₂H₂₅—* Compound 1408 O O C₁₃H₂₇—* C₁₃H₂₇—* Compound 1409 O O C₁₄H₂₉—* C₁₄H₂₉—* Compound 1410 O O C₁₅H₃₁—* C₁₅H₃₁—* Compound 1411 O O C₁₆H₃₃—* C₁₆H₃₃—* Compound 1412 O O C₁₇H₃₅—* C₁₇H₃₅—* Compound 1413 O O C₁₈H₃₇—* C₁₈H₃₇—* Compound 1414 O O p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* Compound 1415 O O p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* Compound 1416 O O p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* Compound 1417 O O p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* Compound 1418 O O p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* Compound 1419 O O p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* Compound 1420 O O p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* Compound 1421 O O p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—*

TABLE 57 X^(c1) X^(c2) R^(c11) R^(c21) Com- O O p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* pound 1422 Com- O O p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* pound 1423 Com- O O p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* pound 1424 Com- O O p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* pound 1425 Com- O O p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* pound 1426 Com- O O p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* pound 1427 Com- pound 1428 O O

Com- pound 1429 O O

Com- pound 1430 O O

Com- pound 1431 O O

Com- pound 1432 O O

Com- pound 1433 O O

Com- pound 1434 O O

Com- pound 1435 O O

Com- pound 1436 O O

Com- pound 1437 O O

Com- pound 1438 O O

Com- pound 1439 O O

Com- pound 1440 O O

Com- pound 1441 O O

Com- S S C₄H₅OC₄H

—* C₄H₅OC

H

—* pound 1442 Com- S S C₂H₃OC

H

—* C₂H₃OC

H₄—* pound 1443

indicates data missing or illegible when filed

TABLE 58 X^(c1) X^(c2) R^(c11) R^(c12) Compound 1444 S S C

H

OC₄H

—* C

H

OC

H

—* Compound 1445 S S C₂H₃OC₄H

—* C₂H

OC₄H

—* Compound 1446 S S CH

OC

H₃—* CH

OC

H

Compound 1447 S S

Compound 1448 S S

Compound 1449 S S

Compound 1450 S S PhC₃H₆—* PhC₃H₆—* Compound 1451 S S PhOC₃H₆—* PhOC₃H₆—* Compound 1452 S S

Compound 1453 S S

Compound 1454 S S

Compound 1455 S S

Compound 1456 S S

Compound 1457 S S 3,7-Dimethyloctyl 3,7-Dimethyloctyl Compound 1458 S S 3,7-Dimethyloctyl H Compound 1459 S S 2-Ethylhexyl 2-Ethylhexyl Compound 1460 S S

Compound 1461 S S

indicates data missing or illegible when filed

TABLE 59 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1462 S S

Compound 1463 S S

H Compound 1464 S S

Compound 1465 S S C₅H₁₁—*

Compound 1466 S S

Compound 1467 S S

Compound 1468 S S

Compound 1469 S S

Compound 1470 S S

Compound 1471 S S

H Compound 1472 S S

Compound 1473 S S

Compound 1474 S S

Compound 1475 S S

In the organic semiconductor layer of the organic semiconductor element according to the present invention or the organic semiconductor film according to the present invention described below, the content of the specific compound is preferably 30 to 100 mass %, more preferably 50 to 100 mass %, and even more preferably 70 to 100 mass %. In a case where a binder polymer described below is not contained, the content is preferably 90 to 100 mass % and more preferably 95 to 100 mass %.

<Binder Polymer>

The organic semiconductor layer of the organic semiconductor element according to the present invention preferably contains the binder polymer.

The organic semiconductor element according to the present invention may be an organic semiconductor element having a layer including the organic semiconductor layer and the binder polymer.

The types of the binder polymer are not particularly limited, and well-known binder polymers can be used.

Examples of the binder polymer include a polystyrene resin, an acrylic resin, rubber, and a thermoplastic elastomer.

Among these, as the binder polymer, a polymer compound (a polymer having a monomer unit having a benzene ring group) having a benzene ring is preferable. The content of the monomer unit having a benzene ring group is not particularly limited. However, the content is preferably 50 mol % or greater, more preferably 70 mol % or greater, and even more preferably 90 mol % or greater with respect to the entire monomer unit. The upper limit is not particularly limited, but examples of the upper limit include 100 mol %.

Examples of the binder polymer include polystyrene, poly(α-methylstyrene), polyvinyl cinnamate, poly(4-vinylphenyl), and poly(4-methylstyrene).

A weight-average molecular weight of the binder polymer is not particularly limited, but is preferably 1,000 to 2,000,000, more preferably 3,000 to 1,000,000, and even more preferably 5,000 to 600,000.

In a case where a solvent described below is used, it is preferable that the binder polymer exhibits solubility higher than the solubility of the specific compound in a used solvent. If the above aspect is adopted, mobility and heat stability of the obtained organic semiconductor are further improved.

A content of the binder polymer in the organic semiconductor layer of the organic semiconductor element of the present invention is preferably 1 to 200 parts by mass, more preferably 10 to 150 parts by mass, and even more preferably 20 to 120 parts by mass with respect to 100 parts by mass of the content of the specific compound. If the content is within the above range, mobility and heat stability of the obtained organic semiconductor are further improved.

<Other Components>

Other components may be included other than the specific compound and the binder polymer may be included in the organic semiconductor layer according to the organic semiconductor element of the present invention.

As other components, known additives and the like can be used.

In the organic semiconductor layer, a content of the components other than the specific compound and the binder polymer is preferably 10 mass % or less, more preferably 5 mass % or less, even more preferably 1 mass % or less, and particularly preferably 0.1 mass % or less. If the content of other components is within the above range, film formability is improved, and mobility and heat stability of the obtained organic semiconductor are further improved.

(Method of Forming Organic Semiconductor Layer)

The method of forming the organic semiconductor layer according to the organic semiconductor element of the present invention is not particularly limited. However, a desired organic semiconductor layer can be formed by applying the composition for forming the organic semiconductor film according to the present invention described below to a source electrode, a drain electrode, and a gate insulating film and performing a drying treatment, if necessary.

(Method of Manufacturing Organic Semiconductor Element and Organic Semiconductor Film)

The organic semiconductor element and an organic semiconductor film of the present invention is preferably manufactured using the composition for forming an organic semiconductor film of the present invention described below.

A method of manufacturing an organic semiconductor film or an organic semiconductor element by using the composition for forming an organic semiconductor film of the present invention is not particularly limited, and known methods can be adopted. Examples thereof include a method of manufacturing an organic semiconductor film by applying the composition onto a predetermined base material and if necessary, performing a drying treatment.

The method of applying the composition onto a base material is not particularly limited, and known methods can be adopted. Examples thereof include an ink jet printing method, a flexographic printing method, a bar coating method, a spin coating method, a knife coating method, a doctor blade method, and the like. Among these, an ink jet printing method and a flexographic printing method are preferable.

Preferred examples of the flexographic printing method include an aspect in which a photosensitive resin plate is used as a flexographic printing plate. By printing the composition onto a substrate according to the aspect, a pattern can be easily formed.

Among these, the method of manufacturing an organic semiconductor element and an organic semiconductor film according to the present invention preferably include an applying step of applying an composition for forming an organic semiconductor film according to the present invention to a substrate and a removing step of removing at least a portion of a solvent having a boiling point of 100° C. or higher included in the composition for forming the organic semiconductor film.

<Solvent Having Boiling Point of 100° C. or Higher>

The composition for forming the organic semiconductor film according to the present invention contains a solvent having a boiling point of 100° C. or higher (hereinafter, referred to a “specific solvent”).

Examples of the specific solvent include a hydrocarbon-based solvent such as octane, decane, toluene, xylene, mesitylene, ethylbenzene, decalin, 1-methylnaphthalene, tetralin, and dimethyltetralin, a ketone-based solvent such as methyl isobutyl ketone and cyclohexanone, a halogenated hydrocarbon-based solvent such as tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, 1-fluoronaphthalene, and 1-chloronaphthalene, an ester-based solvent such as butyl acetate and amyl acetate, an alcohol-based solvent such as butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, and ethylene glycol, an ether-based solvent such as dibutyl ether, dioxane, anisole, 4-tertiary butyl anisole, and m-dimethoxybenzene, an amide-based solvent such as N,N-dimethylformamide and N,N-dimethylacetamide, an imide-based solvent such as 1-methyl-2-pyrrolidone and 1-methyl-2-imidazolidinone, a sulfoxide-based solvent such as dimethyl sulfoxide, and a nitrile-based solvent such as butyronitrile and benzonitrile.

The specific solvent may be used singly or two or more types thereof may be used in combination.

Among these, a hydrocarbon-based solvent, a halogenated hydrocarbon-based solvent and/or an ether-based solvent are preferable, toluene, xylene, mesitylene, tetralin, dichlorobenzene, or anisole is more preferable, and toluene is even more preferable.

If the specific solvent is the aforementioned solvent, coating properties are excellent, and thus an organic semiconductor film can be easily formed.

In view of stability of the composition for forming the organic semiconductor film, forming an even film, and drying, the boiling point of the specific solvent in normal pressure is 100° C. or higher, preferably 100° C. to 300° C., more preferably 100° C. to 200° C., and even more preferably 100° C. to 150° C.

The drying treatment in the removing step is a treatment performed if necessary, and the optimal treatment conditions are suitably selected according to the type of the specific compound used and the solvent. In view of further improving mobility and heat stability of the obtained organic semiconductor and improving productivity, a heating temperature is preferably 30° C. to 100° C. and more preferably 40° C. to 80° C., and a heating time is preferably 10 to 300 minutes and more preferably 30 to 180 minutes.

A thickness of the formed organic semiconductor layer is not particularly limited. From the viewpoint of mobility and heat stability of the obtained organic semiconductor, the film thickness is preferably 10 to 500 nm and more preferably 30 to 200 nm.

<Organic Semiconductor Element>

The organic semiconductor element is not particularly limited, but is preferably an organic semiconductor element having 2 to 5 terminals, and more preferably an organic semiconductor element having 2 or 3 terminals.

It is preferable that the organic semiconductor element is not a photoelectric conversion element.

The organic semiconductor element according to the present invention is preferably a non-luminous organic semiconductor element.

Examples of a 2-terminal element include a rectifier diode, a constant voltage diode, a PIN diode, a Schottky barrier diode, a surge protection diode, a diac, a varistor, a tunnel diode, and the like.

Examples of a 3-terminal element include a bipolar transistor, a Darlington transistor, a field effect transistor, insulated gate bipolar transistor, a uni-junction transistor, a static induction transistor, a gate turn-off thyristor, a triac, a static induction thyristor, and the like.

Among these, a rectifier diode and transistors are preferable, and a field effect transistor is more preferable.

An aspect of the organic thin film transistor of the present invention will be described with reference to drawings.

FIG. 1 is a schematic cross-sectional view of an aspect of an organic semiconductor element (organic thin film transistor (organic TFT)) of the present invention.

In FIG. 1, an organic thin film transistor 100 includes a substrate 10, a gate electrode 20 disposed on the substrate 10, a gate insulating film 30 covering the gate electrode 20, a source electrode 40 and a drain electrode 42 which contact a surface of the gate insulating film 30 that is on the side opposite to the gate electrode 20 side, an organic semiconductor film 50 covering a surface of the gate insulating film 30 between the source electrode 40 and the drain electrode 42, and a sealing layer 60 covering each member. The organic thin film transistor 100 is a bottom gate-bottom contact type organic thin film transistor.

In FIG. 1, the organic semiconductor film 50 corresponds to a film formed of the composition described above.

Hereinafter, the substrate, the gate electrode, the gate insulating film, the source electrode, the drain electrode, the organic semiconductor film, the sealing layer, and methods for forming each of these will be specifically described.

<Substrate>

The substrate plays a role of supporting the gate electrode, the source electrode, the drain electrode, and the like which will be described later.

The type of the substrate is not particularly limited, and examples thereof include a plastic substrate, a glass substrate, a ceramic substrate, and the like. Among these, from the viewpoint of applicability to each device and costs, a glass substrate or a plastic substrate is preferable.

Examples of materials of the plastic substrate include a thermosetting resin (for example, an epoxy resin, a phenol resin, a polyimide resin, or a polyester resin (for example, polyethylene terephthalate (PET) or polyethylene naphthalate (PEN)) and a thermoplastic resin (for example, a phenoxy resin, a polyethersulfone, polysulfone, or polyphenylene sulfone).

Examples of materials of the ceramic substrate include alumina, aluminum nitride, zirconia, silicon, silicon nitride, silicon carbide, and the like.

Examples of materials of the glass substrate include soda lime glass, potash glass, borosilicate glass, quartz glass, aluminosilicate glass, lead glass, and the like.

<Gate Electrode, Source Electrode, and Drain Electrode>

Examples of materials of the gate electrode, the source electrode, and the drain electrode include a metal such as gold (Au), silver, aluminum (Al), copper, chromium, nickel, cobalt, titanium, platinum, tantalum, magnesium, calcium, barium, or sodium; a conductive oxide such as InO₂, SnO₂, or indium tin oxide (ITO); a conductive polymer such as polyaniline, polypyrrole, polythiophene, polyacetylene, or polydiacetylene; a semiconductor such as silicon, germanium, or gallium arsenide; a carbon material such as fullerene, carbon nanotubes, or graphite; and the like. Among these, a metal is preferable, and silver and aluminum are more preferable.

A thickness of each of the gate electrode, the source electrode, and the drain electrode is not particularly limited, but is preferably 20 to 200 nm.

A method of forming the gate electrode, the source electrode, and the drain electrode is not particularly limited, but examples thereof include a method of vacuum vapor-depositing or sputtering an electrode material onto a substrate, a method of coating a substrate with a composition for forming an electrode, a method of printing a composition for forming an electrode onto a substrate, and the like. Furthermore, in a case where the electrode is patterned, examples of the patterning method include a photolithography method; a printing method such as ink jet printing, screen printing, offset printing, or relief printing; a mask vapor deposition method; and the like.

<Gate Insulating Film>

Examples of materials of the gate insulating film include a polymer such as polymethyl methacrylate, polystyrene, polyvinylphenol, polyimide, polycarbonate, polyester, polyvinylalcohol, polyvinyl acetate, polyurethane, polysulfone, polybenzoxazole, polysilsesquioxane, an epoxy resin, or a phenol resin; an oxide such as silicon dioxide, aluminum oxide, or titanium oxide; a nitride such as silicon nitride; and the like. Among these materials, in view of the compatibility with the organic semiconductor film, a polymer is preferable.

In a case where a polymer is used as the material of the gate insulating film, it is preferable to use a cross-linking agent (for example, melamine) in combination. If the cross-linking agent is used in combination, the polymer is cross-linked, and durability of the formed gate insulating film is improved.

A film thickness of the gate insulating film is not particularly limited, but is preferably 100 to 1,000 nm.

A method of forming the gate insulating film is not particularly limited, but examples thereof include a method of coating a substrate, on which the gate electrode is formed, with a composition for forming a gate insulating film, a method of vapor-depositing or sputtering the material of the gate insulating film onto a substrate on which the gate electrode is formed, and the like. A method of coating the aforementioned substrate with the composition for forming a gate insulating film is not particularly limited, and it is possible to use a known method (a bar coating method, a spin coating method, a knife coating method, or a doctor blade method).

In a case where the gate insulating film is formed by coating the substrate with the composition for forming a gate insulating film, for the purpose of removing the solvent, causing cross-linking, or the like, the composition may be heated (baked) after coating.

<Organic Semiconductor Film>

The organic semiconductor film according to the present invention is a film formed of the composition for forming the organic semiconductor film according to the present invention.

The method of forming the organic semiconductor film is not particularly limited. A desired organic semiconductor film can be formed by applying the aforementioned composition to a source electrode, a drain electrode, and a gate insulating film and performing a drying treatment, if desired.

<Binder Polymer Layer>

The organic semiconductor element of the present invention preferably has a layer of the aforementioned binder polymer between the aforementioned organic semiconductor layer and an insulating film, and more preferably has a layer of the aforementioned binder polymer between the aforementioned organic semiconductor layer and the gate insulating film. A film thickness of the binder polymer layer is not particularly limited, but is preferably 20 to 500 nm. The binder polymer layer should be a layer containing the aforementioned polymer, and is preferably a layer composed of the aforementioned binder polymer.

A method of forming the binder polymer layer is not particularly limited, and a known method (a bar coating method, a spin coating method, a knife coating method, a doctor blade method, or an ink jet method) can be used.

In a case where the binder polymer layer is formed by performing coating by using a composition for forming a binder polymer layer, for the purpose of removing a solvent, causing cross-linking, or the like, the composition may be heated (baked) after coating.

<Sealing Layer>

From the viewpoint of durability, the organic semiconductor element of the present invention preferably includes a sealing layer as an outermost layer. In the sealing layer, a known sealant can be used.

A thickness of the sealing layer is not particularly limited, but is preferably 0.2 to 10 μm.

A method of forming the sealing layer is not particularly limited, but examples thereof include a method of coating a substrate, on which the gate electrode, the gate insulating film, the source electrode, the drain electrode, and the organic semiconductor film are formed, with a composition for forming a sealing layer, and the like. Specific examples of the method of coating the substrate with the composition for forming a sealing layer are the same as the examples of the method of coating the substrate with the composition for forming a gate insulating film. In a case where the organic semiconductor film is formed by coating the substrate with the composition for forming a sealing layer, for the purpose of removing the solvent, causing cross-linking, or the like, the composition may be heated (baked) after coating.

FIG. 2 is a schematic cross-sectional view of another aspect of the organic semiconductor element (organic thin film transistor) of the present invention.

In FIG. 2, an organic thin film transistor 200 includes the substrate 10, the gate electrode 20 disposed on the substrate 10, the gate insulating film 30 covering the gate electrode 20, the organic semiconductor film 50 disposed on the gate insulating film 30, the source electrode 40 and the drain electrode 42 disposed on the organic semiconductor film 50, and the sealing layer 60 covering each member. Herein, the source electrode 40 and the drain electrode 42 are formed using the aforementioned composition of the present invention. The organic thin film transistor 200 is a top contact type organic thin film transistor.

The substrate, the gate electrode, the gate insulating film, the source electrode, the drain electrode, the organic semiconductor film, and the sealing layer are as described above.

In FIGS. 1 and 2, the aspects of the bottom gate-bottom contact type organic thin film transistor and the bottom gate-top contact type organic thin film transistor were specifically described. However, the organic semiconductor element of the present invention can also suitably used in a top gate-bottom contact type organic thin film transistor and a top gate-top contact type organic thin film transistor.

The organic thin film transistor described above can be suitably used for electronic paper and a display device.

(Composition for Forming Organic Semiconductor Film)

The composition for forming the organic semiconductor film according to the present invention contains a solvent having a boiling point of 100° C. or higher and a compound represented by Formula 1, and a content of the compound represented by Formula 1 is 20 mass % or less with respect to a total amount of the composition for forming the organic semiconductor film.

The composition for forming the organic semiconductor film according to the present invention preferably contains a binder polymer.

The specific compound, the binder polymer, and the solvent in the composition for forming the organic semiconductor film according to the present invention are the same as the aforementioned specific compound, the aforementioned binder polymer, and the aforementioned solvent, and preferable aspects are also the same.

The content of the specific compound of the composition for forming the organic semiconductor film according to the present invention is 20 mass % or less, preferably 0.001 to 15 mass %, and more preferably 0.01 to 10 mass % with respect to the total amount of the composition for forming the organic semiconductor film. In a case where two or more types of specific compounds are used in combination, the total content of the specific compounds is preferably in the range described above. If the content of the specific compound is in the range described above, the organic semiconductor element having high mobility and high driving stability can be obtained, storage stability of the composition for forming the organic semiconductor film is also satisfactory.

The content of the specific compound is preferably 30 to 100 mass %, more preferably 50 to 100 mass %, and even more preferably 70 to 100 mass % with respect to the total solid content of the composition for forming the organic semiconductor film. In a case where a binder polymer described below is not contained, the total content is preferably 90 to 100 mass % and more preferably 95 to 100 mass %. The solid content is an amount of the component except for the volatile component such as the solvent.

The content of the binder polymer in the composition for forming the organic semiconductor film according to the present invention is preferably greater than 0 mass % and 20 mass % or less, more preferably 0.01 to 15 mass %, and even more preferably 0.25 to 10 mass % with respect to the total amount of the composition for forming the organic semiconductor film. If the content is in the range described above, mobility and heat resistance of the obtained organic semiconductor become more excellent.

The composition for forming the organic semiconductor film according to the present invention may include other component in addition to the specific compound and the binder polymer.

As the component, well-known additives may be used.

The content of the component in addition to the specific compound and the binder polymer in the composition for forming the organic semiconductor film according to the present invention is preferably 10 mass % or less, more preferably 5 mass % or less, even more preferably 1 mass % or less, and particularly preferably 0.1 mass % or less with respect to the total solid content. If the content is in the range described above, film formability is improved, and mobility and heat stability of the obtained organic semiconductor are further improved.

The viscosity of the composition for forming the organic semiconductor film according to the present invention is not particularly limited. However, in view of excellent coating properties, the viscosity is preferably 3 to 100 mPa·s, more preferably 5 to 50 mPa·s, and even more preferably 9 to 40 mPa·s. The viscosity according to the present invention refers to viscosity at 25° C.

As a method of measuring the viscosity, a measuring method in conformity of JIS Z8803 is preferable.

The method of manufacturing the composition for forming the organic semiconductor film according to the present invention is not particularly limited, and well-known methods can be applied. For example, a desired composition can be obtained by adding a specific amount of a specific compound in the solvent and applying an suitable stirring treatment. In a case where the binder polymer is used, the specific compound and the binder polymer are simultaneously or sequentially added, so as to suitably manufacture the composition.

EXAMPLES

Hereinafter, the present invention will be more specifically described based on examples. The materials and the amount thereof used, the proportion of the materials, the content and procedure of treatments, and the like described in the following examples can be suitably changed within a scope that does not depart from the gist of the present invention. Accordingly, the scope of the present invention is not limited to the following specific examples. Herein, unless otherwise specified, “part” and “%” are based on mass.

(Specific Compounds and Synthesis Examples)

Structures of E-1 to E-10 used in the examples and C-1 to C-2 used in the comparative examples are provided below.

<Synthesis of E-1>

An intermediate M1 was synthesized according to a scheme X1 below.

The intermediate M1 and octyl zinc chloride were fused by negishi coupling reaction, so as to synthesize a compound E-1.

<Synthesis of E-2 to E-10>

E-2 to E-10 were also synthesized in the same manner as in E-1, except for changing an organic zinc compound fused with the intermediate M1 to suitable compounds.

<Synthesis of C-1>

A compound C-1 was synthesized according to the method described in JP2010-177637A.

<Synthesis of C-2>

A compound C-2 was synthesized according to the method disclosed in WO2013/168048A.

Examples 1 to 10 and Comparative Examples 1 to 2 Manufacturing of TFT Element

The specific compound presented in Table 60 or a comparative compound (1 mg) and toluene (1 mL) were mixed with each other and heated to 100° C., and the composition for forming the organic semiconductor film was obtained.

An organic semiconductor film was formed by casting this composition to a substrate for measuring FET characteristics which was heated to 90° C. under the nitrogen atmosphere, and an organic thin film transistor element for measuring FET characteristics was obtained. As the substrate for measuring FET characteristics, a silicon substrate in a bottom gate-bottom contact structure including chromium/gold (gate width W=100 mm, gate length L=100 μm) arranged in a comb-shape as source and drain electrodes and SiO₂ (film thickness: 200 nm) as an insulating film was used.

The obtained composition was applied to a substrate for measuring FET characteristics by flexographic printing. Specifically, a flexographic printability test machine F1 (manufactured by IGT Testing Systems) was used as a printing machine, and AFP DSH 1.70% (manufactured by Asahi Kasei Corporation)/a solid image was used as a flexographic resin version. After printing was performed in a pressure between a plate and a substrate of 60 N and a transportation speed of 0.4 m/second, drying was performed at 40° C. for two hours, so as to form an organic semiconductor film, and an organic thin film transistor element (organic TFT element) for measuring FET characteristics was obtained.

As the substrate for measuring FET characteristics, a silicon substrate in a bottom gate-bottom contact structure including chromium/gold (gate width W=100 mm, gate length L=100 μm) arranged in a comb-shape as source and drain electrodes and SiO₂ (film thickness: 200 nm) as an insulating film was used.

The ink was applied to the substrate for measuring FET characteristics by ink jet printing. Specifically, DPP2831 (manufactured by FUJIFILM Global Graphic Systems Co., Ltd.) was used as an inkjet device and 10 pL heads were used, so as to form a solid film with a jetting frequency of 2 Hz and a pitch between dots of 20 μm. Thereafter, drying was performed for one hour at 70° C., so as to form an organic semiconductor film, and the organic TFT element for measuring FET characteristics was obtained.

In the examples and the comparative examples, evaluations of mobility, coating film formability, and heat resistance described below with respect to the organic TFT element obtained by ink jet printing were the same as those of the organic TFT element obtained by casting the composition.

<Carrier Mobility (Mobility)>

With respect to the FET characteristics of the organic thin film transistor elements of the respective examples and the respective comparative examples, carrier mobility was evaluated under normal pressure and the nitrogen atmosphere by employing a semiconductor parameter analyzer (manufactured by Agilent, 4156C) to which a semi automatic prober (manufactured by Vector Semiconductor Co., Ltd., AX-2000) was connected.

A voltage of −80 V was applied between source electrodes and drain electrodes of the respective organic thin film transistor elements (FET elements), a gate voltage was changed in the range of 20 V to −100 V, an equation below presenting a drain current Id was used, so as to calculate carrier mobility μ.

Id=(w/2L)μCi(Vg−Vth)²

In the equation, L represents a gate length, W represents a gate width, Ci represents capacitance of the insulating layer per unit area, Vg represents a gate voltage, and Vth represents a threshold voltage. The numerical value of the carrier mobility is required to be practically 0.01 or greater, preferably 0.1 or greater, and more preferably 0.3 or greater.

The expression “no characteristics” in the tables presents the created element did not have TFT characteristics.

<Coating Film Formability>

The compound according to the present invention or the comparative compound (5 mg) and toluene (1 mL) were mixed and heated to 100° C., so as to obtain a non-luminescent organic semiconductor solution. This coating liquid was casted under nitrogen atmosphere to the entire surface of the substrate which was heated to 90° C. and on which channels for 50 elements were formed, so as to form an organic semiconductor thin film, and 50 organic thin film transistor elements for measuring FET characteristics were obtained. Evaluation standards of the coating film formability were set as below, and the evaluation results were presented in Table 60.

[Evaluation standard] A: 45 or more elements out of the obtained 50 elements were driven as organic thin film transistor element

B: Less than 45 elements out of the obtained 50 elements were driven as organic thin film transistor element

<Heat Resistance>

After the manufactured respective organic thin film transistor elements were heated for one hour at 130° C. in a nitrogen glove box, carrier mobility μ was measured, so as to calculate a carrier mobility maintenance rate after heating by the equation below.

Carrier mobility maintenance rate after heating (%)=Carrier mobility (after heating)/carrier mobility (initial value)×100

Obtained results were evaluated according to evaluation standards below. The evaluation results are presented in Table 60. The expression “N/A” in the table means that a heat resistance was not performed since a created element did not have TFT characteristics.

[Evaluation Standard]

A: Carrier mobility maintenance rate after heating was 95% or greater

B: Carrier mobility maintenance rate after heating was 70% or greater and less than 95%

C: Carrier mobility maintenance rate after heating was 40% or greater and less than 70%

D: Carrier mobility maintenance rate after heating was 20% or greater and less than 40%

E: Carrier mobility maintenance rate after heating was less than 20%

TABLE 60 Specific Solu- Coating film Heat compound Mobility bility formability resistance Example 1 E-1 1.1 A A A Example 2 E-2 1 B A A Example 3 E-3 0.5 A A A Example 4 E-4 0.7 B A A Example 5 E-5 0.6 A A B Example 6 E-6 0.3 A A A Example 7 E-7 0.05 B A A Example 8 E-8 0.03 B A B Example 9 E-9 0.03 C A A Example 10 E-10 0.01 B A A Comparative C-1 No C B N/A Example 1 Charac- teristics Comparative C-2 5 × 10⁻³ C B D Example 2

Examples 11 to 16, Comparative Examples 3 to 4 Manufacturing of TFT Elements

Respective evaluations were performed in the same manner as in Examples 1 to 10 and Comparative Examples 1 to 2 except for mixing the specific compound of the present invention or the comparative compound presented in Table 61, the binder polymer presented in Table 61, and the solvent presented in Table 61 in the concentrations presented in Table 61, performing heating to 100° C., and using the resultant as the composition for forming the organic semiconductor film. The respective evaluation results are presented in Table 61.

Abbreviations used in Table 61 are as below.

-   -   PαMS: Poly(α-methylstyrene), Mw=300,000, manufactured by         Sigma-Aldrich Co. LLC.)     -   THF: Tetrahydrofuran

TABLE 61 Concentration Concentration of of binder semiconductor in polymer in Coating Specific Binder composition composition Heat film compound polymer Solvent (mass %) (mass %) Mobility resistance formability Example 11 E-1 PαMS Toluene 0.5 0.5 1.2 A A Example 12 E-2 PαMS Toluene 0.5 0.5 1.2 A A Example 13 E-5 PαMS Toluene 0.5 0.5 0.8 A A Example 14 E-6 PαMS Toluene 0.5 0.5 0.5 A A Example 15 E-1 PαMS THF 0.5 0.5 0.1 B A Example 16 E-1 PαMS Toluene 0.5 12.0 0.02 B A Comparative C-1 PαMS Toluene 0.5 0.5 2 × 10⁻³ D B Example 3 Comparative C-2 PαMS Toluene 0.5 0.5 No N/A B Example 4 characteristics

Comparative Examples 5 to 21

The organic semiconductor films were formed in the same manner as in Example 1 to 16 except for weighing the specific compounds and toluene (1 mL) presented in Tables 60 and 61 and further the binder polymer (5 mg) in the examples presented in Table 61 such that the content of the respective specific compounds become 21 mass %, performing mixture, performing heating to 100° C., and using the resultant as the composition for forming the organic semiconductor film. However, in all of Comparative Examples 5 to 21, due to insoluble matters, various defects were generated, and thus TFT characteristics were not exhibited.

EXPLANATION OF REFERENCES

-   -   10: substrate     -   20: gate electrode     -   30: gate insulating film     -   40: source electrode     -   42: drain electrode     -   50: organic semiconductor film     -   60: sealing layer     -   100,200: organic thin film transistor 

What is claimed is:
 1. An organic semiconductor element comprising: a compound represented by Formula 1 below in an organic semiconductor layer,

in Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom, Z^(1a) to Z^(1j) each independently represent a hydrogen atom or a halogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom, R^(A11) represents a hydrogen atom or a group represented by R¹¹, A¹² represents ═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogen atom or a group represented by R¹², n1 represents 0 or 1, p1 represents an integer of 0 to 2 in a case where A¹¹ is —CR^(A11)— and represents 0 or 1 in a case where A¹¹ is a nitrogen atom, q1 represents an integer of 0 to 2 in a case where A¹² is ═CR^(A12)— and represents 0 or 1 in a case where A¹² is a nitrogen atom, R¹¹ and R¹² each independently represent a halogen atom, an aryl group, a heteroaryl group, or a group represented by Formula W below, -S^(W)-L^(W)-T^(W)  (W) in Formula W, S^(W) represents a single bond or an alkylene group represented by —(CR^(S) ₂)_(k)—, R^(S) each independently represent a hydrogen atom or a halogen atom, k represents an integer of 1 to 17, L^(W) represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-16 below, or a group obtained by bonding any two or more of divalent linking groups represented by Formulae L-1 to L-16 below, T^(W) represents an alkyl group, a cyano group, a vinyl group, an ethynyl group, an aryl group, a heteroaryl group, an oxyethylene group, an oligooxyethylene group of which the repetition number of oxyethylene units is two or greater, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group, and

in Formulae L-1 to L-16, * and wavy line portions represent bonding positions to other structures, p13 represents an integer of 0 to 4, p14, p15, and p16 each independently represent an integer of 0 to 2, R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) each independently represent a hydrogen atom or a substituent.
 2. The organic semiconductor element according to claim 1, wherein all of Z^(1a) to Z^(1j) are hydrogen atoms.
 3. The organic semiconductor element according to claim 1, wherein n1 is not
 0. 4. The organic semiconductor element according to claim 1, wherein at least one of p1 or q1 is not
 0. 5. The organic semiconductor element according to claim 1, wherein at least one of p1 or q1 is not 0, and at least one of R¹¹ or R¹² is a group represented by Formula W.
 6. The organic semiconductor element according to claim 1, wherein p1 and q1 are
 1. 7. The organic semiconductor element according to claim 1, wherein both of X¹¹ and X¹² are S atoms, A¹¹ is ═CR^(A11)—, and A¹² is ═CR^(A12)—.
 8. The organic semiconductor element according to claim 1, wherein a compound represented by Formula 1 is a compound represented by Formula 2 below,

in Formula 2, X²¹ and X²² each independently represent a chalcogen atom, W²¹ and W²² each independently represent a group represented by Formula W.
 9. The organic semiconductor element according to claim 1, wherein the compound represented by Formula 1 is a line symmetric structure.
 10. The organic semiconductor element according to claim 1, wherein the number of carbon atoms in the group represented by Formula W is 5 to
 40. 11. The organic semiconductor element according to claim 1, wherein L^(W) is a single bond, a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16, or a divalent linking group obtained by bonding two or more divalent linking groups represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.
 12. The organic semiconductor element according to claim 1, wherein L^(W) is a single bond or a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.
 13. The organic semiconductor element according to claim 1, wherein S^(W) is a single bond.
 14. The organic semiconductor element according to claim 1, wherein L^(W) is a single bond or a divalent linking group represented by any one of Formula L-1 and Formulae L-13 to L-16.
 15. The organic semiconductor element according to claim 1, wherein T^(W) is an alkyl group.
 16. The organic semiconductor element according to claim 1, wherein a group represented by Formula W is an alkyl group.
 17. A composition for forming an organic semiconductor film, comprising: a solvent having a boiling point of 100° C. or higher, and a compound represented by Formula 1, wherein a content of the compound represented by Formula 1 is 20 mass % or less with respect to a total amount of the composition for forming an organic semiconductor film,

in Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom, Z^(1a) to Z^(1j) each independently represent a hydrogen atom or a halogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom, R^(A11) represents a hydrogen atom or a group represented by R¹¹, A¹² represents ═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogen atom or a group represented by R¹², n1 represents 0 or 1, p1 represents an integer of 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0 or 1 in a case where A¹¹ is a nitrogen atom, q1 represents an integer of 0 to 2 in a case where A¹² is ═CR^(A12)—, and represents 0 or 1 in a case where A¹² is a nitrogen atom, R¹¹ and R¹² each independently represent a halogen atom, an aryl group, a heteroaryl group, or a group represented by Formula W below, -S^(W)-L^(W)-T^(W)  (W) in Formula W, S^(W) represents a single bond or an alkylene group represented by —(CR^(S) ₂)_(k)—, R^(S) each independently represent a hydrogen atom or a halogen atom, k represents an integer of 1 to 17, L^(W) represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-16 below, or a group obtained by bonding any two or more of divalent linking groups represented by Formulae L-1 to L-16 below, T^(W) represents an alkyl group, a cyano group, a vinyl group, an ethynyl group, an aryl group, a heteroaryl group, an oxyethylene group, an oligooxyethylene group of which the repetition number of oxyethylene units is two or greater, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group, and

in Formulae L-1 to L-16, * and wavy line portions represent bonding positions to other structures, p13 represents an integer of 0 to 4, p14, p15, and p16 each independently represent an integer of 0 to 2, R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) each independently represent a hydrogen atom or a substituent.
 18. The composition for forming an organic semiconductor film according to claim 17, wherein all of Z^(1a) to Z^(1j) are hydrogen atoms.
 19. The composition for forming an organic semiconductor film according to claim 17, wherein n1 is
 0. 20. The composition for forming an organic semiconductor film according to claim 17, wherein at least one of p1 or q1 is not
 0. 21. The composition for forming an organic semiconductor film according to claim 17, wherein at least one of p1 or q1 is not 0, and at least one of R or R¹² is a group represented by Formula W.
 22. The composition for forming an organic semiconductor film according to claim 17, wherein p1 and q1 is
 1. 23. The composition for forming an organic semiconductor film according to claim 17, wherein both of X¹¹ and X¹² are S atoms, A¹¹ is ═CR^(A11)—, and A¹² is —CR^(A12).
 24. The composition for forming an organic semiconductor film according to claim 17, wherein the compound represented by Formula 1 is a compound represented by Formula 2 below,

in Formula 2, X²¹ and X²² each independently represent a chalcogen atom, W²¹ and W²² each independently represent a group represented by Formula W.
 25. The composition for forming an organic semiconductor film according to claim 17, wherein the compound represented by Formula 1 is a line symmetric structure.
 26. The composition for forming an organic semiconductor film according to claim 17, wherein the number of carbon atoms in the group represented by Formula W is 5 to
 40. 27. The composition for forming an organic semiconductor film according to claim 17, wherein L^(W) is a single bond, a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16, and a divalent linking group obtained by bonding two or more divalent linking groups represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.
 28. The composition for forming an organic semiconductor film according to claim 17, wherein L^(W) is a single bond or a divalent linking group represented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.
 29. The composition for forming an organic semiconductor film according to claim 17, wherein S^(W) is a single bond.
 30. The composition for forming an organic semiconductor film according to claim 17, wherein L^(W) is a single bond or a divalent linking group represented by any one of Formula L-1 and Formulae L-13 to L-16.
 31. The composition for forming an organic semiconductor film according to claim 17, wherein T^(W) is an alkyl group.
 32. The composition for forming an organic semiconductor film according to claim 17, wherein a group represented by Formula W is an alkyl group.
 33. The composition for forming an organic semiconductor film according to claim 17, further comprising: a binder polymer, wherein a content of the binder polymer is 10 mass % or less with respect to a total amount of the composition for forming an organic semiconductor film.
 34. A compound represented by Formula 1 below,

in Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom, Z^(1a) to Z^(1j) each independently represent a hydrogen atom or a halogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom, R^(A11) represents a hydrogen atom or a group represented by R¹¹, A¹² represents ═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogen atom or a group represented by R¹², n1 represents 0 or 1, p1 represents an integer of 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0 or 1 in a case where A¹¹ is a nitrogen atom, q1 represents an integer of 0 to 2 in a case where A¹² is ═CR^(A12)— and represents 0 or 1 in a case where A¹² is a nitrogen atom, R¹¹ and R¹² each independently represent a halogen atom, an aryl group, a heteroaryl group, or a group represented by Formula W below, -S^(W)-L^(W)-T^(W)  (W) in Formula W, S^(W) represents a single bond or an alkylene group represented by —(CR^(S) ₂)_(k)—, R^(S) each independently represent a hydrogen atom or a halogen atom, k represents an integer of 1 to 17, L^(W) represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-16 below, or a group obtained by bonding any two or more of divalent linking groups represented by Formulae L-1 to L-16 below, T^(W) represents an alkyl group, a cyano group, a vinyl group, an ethynyl group, an aryl group, a heteroaryl group, an oxyethylene group, an oligooxyethylene group of which the repetition number of oxyethylene units is two or greater, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group, and

in Formulae L-1 to L-16, * and wavy line portions represent bonding positions to other structures, p13 represents an integer of 0 to 4, p14, p15, and p16 each independently represent an integer of 0 to 2, R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) each independently represent a hydrogen atom or a substituent.
 35. A method of manufacturing an organic semiconductor film, comprising: an applying step of applying the composition for forming an organic semiconductor film according to claim 17 to a substrate, and a removing step of removing at least a portion of the solvent having a boiling point of 100° C. or higher included in the composition for forming an organic semiconductor film.
 36. The method of manufacturing the organic semiconductor film according to claim 35, wherein the applying step is performed by an ink jet method or a flexographic printing method.
 37. An organic semiconductor film obtained by the method according to claim
 35. 38. A method of manufacturing an organic semiconductor element, comprising: an applying step of applying the composition for forming an organic semiconductor film according to claim 17 to a substrate, and a removing step of removing at least a portion of the solvent having a boiling point of 100° C. or higher included in the composition for forming an organic semiconductor film.
 39. The method of manufacturing the organic semiconductor element according to claim 38, wherein the applying step is performed by an ink jet method or a flexographic printing method.
 40. An organic semiconductor element manufactured by the method according to claim
 38. 